Insecticidal anthranilamides

ABSTRACT

This invention provides compounds of Formula (1), their N-oxides and agriculturally suitable salts wherein A, B, J, R 1 , R 2 , R 3  and R 4  and n are as defined in the disclosure. Also disclosed are methods for controlling arthropods comprising contacting the arthropods or their environment with an arthropodicidally effective amount of a compound of Formula (1) and compositions containing the compounds of Formula (1).

This application is a 35 U.S.C. 371 national stage entry from International Application No. PCT/US01/09338, filed Mar. 20, 2001 which claims priority benefit from U.S. Provisional Application No. 60/191,242, filed Mar. 22, 2000, U.S. Provisional Application No. 60/220,232, filed Jul. 24, 2000, U.S. Provisional Application No. 60/254,635, filed Dec. 11, 2000, and U.S. Provisional Application No. 60/262,015, filed Jan. 17, 2001.

BACKGROUND OF THE INVENTION

This invention relates to certain anthranilamides, their N-oxides, agriculturally suitable salts and compositions, and methods of their use as arthropodicides in both agronomic and nonagronomic environments.

The control of arthropod pests is extremely important in achieving high crop efficiency. Arthropod damage to growing and stored agronomic crops can cause significant reduction in productivity and thereby result in increased costs to the consumer. The control of arthropod pests in forestry, greenhouse crops, ornamentals, nursery crops, stored food and fiber products, livestock, household, and public and animal health is also important. Many products are commercially available for these purposes, but the need continues for new compounds that are more effective, less costly, less toxic, environmentally safer or have different modes of action.

NL 9202078 discloses N-acyl anthranilic acid derivatives of Formula i as insecticides

wherein, inter alia,

X is a direct bond;

Y is H or C₁-C₆ alkyl;

Z is NH₂, NH(C₁-C₃ alkyl) or N(C₁-C₃ alkyl)₂; and

R¹ through R⁹ are independently H, halogen, C₁-C₆ alkyl, phenyl, hydroxy, C₁-C₆ alkoxy or C₁-C₇ acyloxy.

SUMMARY OF THE INVENTION

This invention pertains to a method for controlling arthropods comprising contacting the arthropods or their environment with an arthropodicidally effective amount of a compound of Formula 1, its N-oxide or agriculturally suitable salts

wherein

A and B are independently O or S;

each J is independently a phenyl or naphthyl group substituted with 1 to 2 R⁵ and optionally substituted with 1 to 3 R⁶;

or each J is independently a 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system wherein each ring or ring system is optionally substituted with 1 to 4 R⁷;

n is 1 to 4;

R¹ is H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆ cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₄ alkoxycarbonyl C₁-C₄ alkylamino, C₂-C₈ dialkylamino and C₃-C₆ cycloalkylamino; or

R¹ is C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C(═A)J;

R² is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ alkoxy, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆ alkoxycarbonyl or C₂-C₆ alkylcarbonyl;

R³ is H; G; C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, each optionally substituted with one or more substituents selected from the group consisting of halogen, G, CN, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylcarbonyl, C₃-C₆ trialkylsilyl, and a phenyl, phenoxy or 5- or 6-membered heteroaromatic ring, each ring optionally substituted with one to three substituents independently selected from the group consisting of C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl and C₃-C₆ trialkylsilyl; C₁-C₄ alkoxy; C₁-C₄ alkylamino; C₂-C₈ dialkylamino; C₃-C₆ cycloalkylamino; C₂-C₆ alkoxycarbonyl or C₂-C₆ alkylcarbonyl; or

R² and R³ can be taken together with the nitrogen to which they are attached to form a ring containing 2 to 6 atoms of carbon and optionally one additional atom of nitrogen, sulfur or oxygen, said ring may be optionally substituted with 1 to 4 substituents selected from the group consisting of C₁-C₂ alkyl, halogen, CN, NO₂ and C₁-C₂ alkoxy;

G is a 5- or 6-membered nonaromatic carbocyclic or heterocyclic ring, optionally including one or two ring members selected from the group consisting of C(═O), SO or S(O)₂ and optionally substituted with 1 to 4 substituents selected from the group consisting of C₁-C₂ alkyl, halogen, CN, NO₂ and C₁-C₂ alkoxy;

each R⁴ is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, or C₃-C₆ trialkylsilyl; or

each R⁴ is independently phenyl, benzyl or phenoxy, each optionally substituted with C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl;

each R⁵ is independently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, CO₂H, CONH₂, NO₂, hydroxy, C₁-C₆ alkoxy, C₁-C₆ haloalkoxy, C₁-C₆ alkylthio, C₁-C₆ alkylsulfinyl, C₁-C₆ alkylsulfonyl, C₁-C₆ haloalkylthio, C₁-C₆ haloalkylsulfinyl, C₁-C₆ haloalkylsulfonyl, C₁-C₆ alkylamino, C₂-C₁₂ dialkylamino, or C₃-C₆ cycloalkylamino, C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl, C₃-C₆ trialkylsilyl; or

(R⁵)₂ when attached to adjacent carbon atoms can be taken together as —OCF₂O—, —CF₂CF₂O—, or —OCF₂CF₂O—;

each R⁶ is independently H, halogen, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ alkoxy or C₂-C₄ alkoxycarbonyl; or

each R⁶ is independently a phenyl, benzyl, phenoxy, 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, each ring optionally substituted with one to three substituents independently selected from the group consisting of C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl;

each R⁷ is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, CO₂H, CONH₂, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl, or C₃-C₆ trialkylsilyl; or

each R⁷ is independently a phenyl, benzyl, benzoyl, phenoxy, 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, each ring optionally substituted with one to three substituents independently selected from the group consisting of C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl and C₃-C₆ trialkylsilyl;

provided that

(1) when A and B are both O, R² is H or C₁-C₃ alkyl, R³ is H or C₁-C₃ alkyl and R⁴ is H, halogen, C₁-C₆ alkyl, phenyl, hydroxy or C₁-C₆ alkoxy, then one R⁵ is other than halogen, C₁-C₆ alkyl, hydroxy or C₁-C₆ alkoxy; or

(2) J is other than an optionally substituted 1,2,3-thiadiazole.

This invention also pertains to compounds of Formula 1, their N-oxides and agriculturally suitable salts

wherein

A and B are independently O or S;

each J is independently a phenyl or naphthyl group substituted with 1 to 2 R⁵ and optionally substituted with 1 to 3 R⁶;

or each J is independently a 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system wherein each ring or ring system is optionally substituted with 1 to 4 R⁷;

n is 1 to 4;

R¹ is H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆ cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₄ alkoxycarbonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino and C₃-C₆ cycloalkylamino; or

R¹ is C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C(═A)J;

R² is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ alkoxy, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆ alkoxycarbonyl or C₂-C₆ alkylcarbonyl;

R³ is H; C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylcarbonyl, C₃-C₆ trialkylsilyl, and a phenoxy ring optionally substituted with one to three substituents independently selected from the group consisting of C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl and C₃-C₆ trialkylsilyl; C₁-C₄ alkoxy; C₁-C₄ alkylamino; C₂-C₈ dialkylamino; C₃-C₆ cycloalkylamino; C₂-C₆ alkoxycarbonyl or C₂-C₆ alkylcarbonyl; or

R² and R³ can be taken together with the nitrogen to which they are attached to form a ring containing 2 to 6 atoms of carbon and optionally one additional atom of nitrogen, sulfur or oxygen, said ring may be optionally substituted with 1 to 4 substituents selected from the group consisting of C₁-C₂ alkyl, halogen, CN, NO₂ and C₁-C₂ alkoxy;

each R⁴ is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl. C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, or C₃-C₆ trialkylsilyl; or

each R⁴ is independently phenyl, benzyl or phenoxy, each optionally substituted with C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl;

each R⁵ is independently C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, CN, NO₂, C₁-C₄ alkoxycarbonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, or C₃-C₈ dialkylaminocarbonyl; or

(R⁵)₂ attached to adjacent carbon atoms can be taken together as —OCF₂O—, —CF₂CF₂O—, or —OCF₂CF₂O—;

each R⁶ is independently H, halogen, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ alkoxy or C₂-C₄ alkoxycarbonyl; or

each R⁶ is independently a phenyl, benzyl, phenoxy, 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, each ring optionally substituted with one to three substituents independently selected from the group consisting of C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl;

each R⁷ is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, CO₂H, CONH₂, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl, or C₃-C₆ trialkylsilyl; or

each R⁷ is independently a phenyl, benzyl, benzoyl, phenoxy or 5- or 6-membered heteroaromatic ring or an 8-, 9- or 10-membered fused heterobicyclic ring system, each ring optionally substituted with one to three substituents independently selected from the group consisting of C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl and C₃-C₆ trialkylsilyl;

provided that

(i) at least one R⁴ and at least one R⁷ are other than H;

(ii) J is other than an optionally substituted 1,2,3-thiadiazole;

(iii) when J is an optionally substituted pyridine and R² is H, R³ is other than H or CH₃;

(iv) when J is an optionally substituted pyridine, then R⁷ cannot be CONH₂, C₂-C₆ alkylaminocarbonyl or C₃-C₈ dialkylaminocarbonyl;

(v) when J is an optionally substituted pyrazole, tetrazole or pyrimidine, then R² and R³ cannot both be hydrogen.

This invention also pertains to arthropodicidal compositions comprising an arthropodicidally effective amount of a compound of Formula 1 and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents.

DETAILS OF THE INVENTION

In the above recitations, the term “alkyl”, used either alone or in compound words such as “alkylthio” or “haloalkyl” includes straight-chain or branched alkyl, such as, methyl, ethyl, n-propyl, i-propyl, or the different butyl, pentyl or hexyl isomers. The term “1-2 alkyl” indicates that one or two of the available positions for that substituent may be alkyl. “Alkenyl” includes straight-chain or branched alkenes such 1-propenyl, 2-propenyl, and the different butenyl, pentenyl and hexenyl isomers. “Alkenyl” also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. “Alkynyl” includes straight-chain or branched alkynes such as 1-propynyl, 2-propynyl and the different butynyl, pentynyl and hexynyl isomers. “Alkynyl” can also include moieties comprised of multiple triple bonds such as 2,5-hexadiynyl. “Alkoxy” includes, for example, methoxy, ethoxy, n-propyloxy, isopropyloxy and the different butoxy, pentoxy and hexyloxy isomers. “Alkoxyalkyl” denotes alkoxy substitution on alkyl. Examples of “alkoxyalkyl” include CH₃OCH₂, CH₃OCH₂CH₂, CH₃CH₂OCH₂, CH₃CH₂CH₂CH₂OCH₂ and CH₃CH₂OCH₂CH₂. “Alkylthio” includes branched or straight-chain alkylthio moieties such as methylthio, ethylthio, and the different propylthio, butylthio, pentylthio and hexylthio isomers. “Cycloalkyl” includes, for example, cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

The term “heterocyclic ring” or heterocyclic ring system” denotes rings or ring systems in which at least one ring atom is not carbon and comprises 1 to 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that each heterocyclic ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs. The heterocyclic ring can be attached through any available carbon or nitrogen by replacement of hydrogen on said carbon or nitrogen. The term “aromatic ring system” denotes fully unsaturated carbocycles and heterocycles in which the polycyclic ring system is aromatic (where aromatic indicates that the Hückel rule is satisfied for the ring system). The term “heteroaromatic ring” denotes fully aromatic rings in which at least one ring atom is not carbon and comprises 1 to 4 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that each heterocyclic ring contains no more than 4 nitrogens, no more than 2 oxygens and no more than 2 sulfurs (where aromatic indicates that the Hückel rule is satisfied). The heterocyclic ring can be attached through any available carbon or nitrogen by replacement of hydrogen on said carbon or nitrogen. The term “aromatic heterocyclic ring system” includes fully aromatic heterocycles and heterocycles in which at least one ring of a polycyclic ring system is aromatic (where aromatic indicates that the Hückel rule is satisfied). The term “fused heterobicyclic ring system” includes a ring system comprised of two fused rings in which at least one ring atom is not carbon and can be aromatic or non aromatic, as defined above.

The term “halogen”, either alone or in compound words such as “haloalkyl”, includes fluorine chlorine bromine or iodine. Further, when used in compound words such as “haloalkyl”, said alkyl may be partially or fully substituted with halogen atoms which may be the same or different. Examples of “haloalkyl” include F₃C, ClCH₂, CF₃CH₂ and CF₃CCl₂. The terms “haloalkenyl”, “haloalkynyl”, “haloalkoxy”, and the like, are defined analogously to the term “haloalkyl”. Examples of “haloalkenyl” include (Cl)₂C═CHCH₂ and CF₃CH₂CH═CHCH₂. Examples of “haloalkynyl” include HC≡CCHCl, CF₃C≡C, CCl₃C≡C and FCH₂C≡CCH₂. Examples of “haloalkoxy” include CF₃O, CCl₃CH₂O, HCF₂CH₂CH₂O and CF₃CH₂O.

The total number of carbon atoms in a substituent group is indicated by the “C_(i)-C_(j)” prefix where i and j are numbers from 1 to 6. For example, C₁-C₃ alkylsulfonyl designates methylsulfonyl through propylsulfonyl; C₂ alkoxyalkyl designates CH₃OCH₂; C₃ alkoxyalkyl designates, for example, CH₃CH(OCH₃), CH₃OCH₂CH₂ or CH₃CH₂OCH₂; and C₄ alkoxyalkyl designates the various isomers of an alkyl group substituted with an alkoxy group containing a total of four carbon atoms, examples including CH₃CH₂CH₂OCH₂ and CH₃CH₂OCH₂CH₂. In the above recitations, when a compound of Formula 1 contains a heterocyclic ring, all substituents are attached to this ring through any available carbon or nitrogen by replacement of a hydrogen on said carbon or nitrogen.

When a group contains a substituent which can be hydrogen, for example R³, then, when this substituent is taken as hydrogen, it is recognized that this is equivalent to said group being unsubstituted.

Compounds of this invention can exist as one or more stereoisomers. The various stereoisomers include enantiomers, diastereomers, atropisomers and geometric isomers. One skilled in the art will appreciate that one stereoisomer may be more active and/or may exhibit beneficial effects when enriched relative to the other stereoisomer(s) or when separated from the other stereoisomer(s). Additionally, the skilled artisan knows how to separate, enrich, and/or to selectively prepare said stereoisomers. Accordingly, the compounds of the invention may be present as a mixture of stereoisomers, individual stereoisomers, or as an optically active form.

The present invention comprises compounds selected from Formula 1, N-oxides and agriculturally suitable salts thereof. One skilled in the art will appreciate that not all nitrogen containing heterocycles can form N-oxides since the nitrogen requires an available lone pair for oxidation to the oxide; one skilled in the art will recognize those nitrogen containing heterocycles which can form N-oxides. One skilled in the art will also recognize that tertiary amines can form N-oxides. Synthetic methods for the preparation of N-oxides of heterocycles and tertiary amines are very well known by one skilled in the art including the oxidation of heterocycles and tertiary amines with peroxy acids such as peracetic and m-chloroperbenzoic acid (MCPBA), hydrogen peroxide, alkyl hydroperoxides such as t-butyl hydroperoxide, sodium perborate, and dioxiranes such as dimethydioxirane. These methods for the preparation of N-oxides have been extensively described and reviewed in the literature, see for example: T. L. Gilchrist in Comprehensive Organic Synthesis, vol. 7, pp 748-750, S. V. Ley, Ed., Pergamon Press; M. Tisler and B. Stanovnik in Comprehensive Heterocyclic Chemistry, vol. 3, pp 18-19, A. J. Boulton and A. McKillop, Eds., Pergamon Press; M. R. Grimmett and B. R. T. Keene in Advances in Heterocyclic Chemistry, vol. 43, pp 139-151, A. R. Katritzky, Ed., Academic Press; M. Tisler and B. Stanovnik in Advances in Heterocyclic Chemistry, vol. 9, pp 285-291, A. R. Katritzky and A. J. Boulton, Eds., Academic Press; and G. W. H. Cheeseman and E. S. G. Werstiuk in Advances in Heterocyclic Chemistry, vol. 22, pp 390-392, A. R. Katritzky and A. J. Boulton, Eds., Academic Press.

The salts of the compounds of the invention include acid-addition salts with inorganic or organic acids such as hydrobromic, hydrochloric, nitric, phosphoric, sulfuric, acetic, butyric, fumaric, lactic, maleic, malonic, oxalic, propionic, salicylic, tartaric, 4-toluenesulfonic or valeric acids.

Of note are certain compounds of Formula II

wherein

X and Y are O;

m is 1 to 5;

n is 1 to 4;

R¹ is H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆ cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₄ alkoxycarbonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino and C₃-C₆ cycloalkylamino; or

R¹ is C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl or C₃-C₈ dialkylaminocarbonyl;

R² is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ alkoxy, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆ alkoxycarbonyl or C₂-C₆ alkylcarbonyl;

R³ is i-propyl or t-butyl; and

each R⁴ and R⁵ are independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, CO₂H, CONH₂, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkoxycarbonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl, C₃-C₆ trialkylsilyl; or

each R⁴ and R⁵ are independently phenyl optionally substituted with C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl C₁-C₄ alkoxycarbonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl.

Also of note are methods for controlling arthropods comprising contacting the arthropods or their environment with an arthropodicidally effective amount of a compound of Formula II and insecticidal compositions thereof.

Also of note are certain compounds of Formula III

wherein

A and B are independently O or S;

J is a phenyl group substituted with 1 to 2 R⁵ and optionally substituted with 1 to 3 R⁶, or a 5- or 6-membered heteroaromatic ring optionally substituted with 1 to 4 R⁷;

n is 1 to 4;

R¹ is H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆ cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₄ alkoxycarbonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino and C₃-C₆ cycloalkylamino; or

R¹ is C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl or C₃-C₈ dialkylaminocarbonyl;

R² is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ alkoxy, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆ alkoxycarbonyl or C₂-C₆ alkylcarbonyl;

R³ is H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆ cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl and C₁-C₄ alkylsulfonyl; or

R² and R³ can be taken together with the nitrogen to which they are attached to form a ring containing 2 to 6 atoms of carbon and optionally one additional atom of nitrogen, sulfur or oxygen, said ring may be optionally substituted with 1 to 4 substituents selected from the group consisting of C₁-C₂ alkyl, halogen, CN, NO₂ and C₁-C₂ alkoxy;

each R⁴ is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, CO₂H, CONH₂, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl, C₃-C₆ trialkylsilyl; or

each R⁴ is independently phenyl, benzyl or phenoxy, each optionally substituted with C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl;

each R⁵ is independently C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, CN, NO₂, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, or C₃-C₈ dialkylaminocarbonyl; or

(R⁵)₂ when attached to adjacent carbon atoms can be taken together as —OCF₂O—, —CF₂CF₂O—, or —OCF₂CF₂O—;

each R⁶ is independently H, halogen, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ alkoxy; or

each R⁶ is independently phenyl, benzyl or phenoxy, each optionally substituted with C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl;

each R⁷ is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, CO₂H, CONH₂, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl, C₃-C₆ trialkylsilyl; or

each R⁷ is independently phenyl, benzyl or phenoxy, each optionally substituted with C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl C₁-C₄ alkoxycarbonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl.

Also of note are methods for controlling arthropods comprising contacting the arthropods or their environment with an arthropodicidally effective amount of a compound of Formula III and insecticidal compositions thereof.

Also of note are certain compounds of Formula IV

wherein

A and B are independently O or S;

J is a phenyl group substituted with 1 to 2 R⁵ and optionally substituted with 1 to 3 R⁶, or a 5- or 6-membered heteroaromatic ring optionally substituted with 1 to 4 R⁷;

n is 1 to 4;

R¹ is H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆ cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₄ alkoxycarbonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino and C₃-C₆ cycloalkylamino; or

R¹ is C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl or C₃-C₈ dialkylaminocarbonyl;

R² is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ alkoxy, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆ alkoxycarbonyl or C₂-C₆ alkylcarbonyl;

R³ is H; C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl and C₁-C₄ alkylsulfonyl; C₁-C₄ alkoxy; C₁-C₄ alkylamino; C₂-C₈ dialkylamino; C₃-C₆ cycloalkylamino; C₂-C₆ alkoxycarbonyl or C₂-C₆ alkylcarbonyl; or

R² and R³ can be taken together with the nitrogen to which they are attached to form a ring containing 2 to 6 atoms of carbon and optionally one additional atom of nitrogen sulfur or oxygen, said ring may be optionally substituted with 1 to 4 substituents selected from the group consisting of C₁-C₂ alkyl, halogen, CN, NO₂ and C₁-C₂ alkoxy;

each R⁴ is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, CO₂H, CONH₂, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl, C₃-C₆ trialkylsilyl; or

each R⁴ is independently phenyl, benzyl or phenoxy, each optionally substituted with C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl;

each R⁵ is independently C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, CO₂H, CONH₂, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl, C₃-C₆ trialkylsilyl; or

(R⁵)₂ when attached to adjacent carbon atoms can be taken together as —OCF₂O—, —CF₂CF₂O—, or —OCF₂CF₂O—;

each R⁶ is independently H, halogen, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ alkoxy; or

each R⁶ is independently a phenyl, benzyl, phenoxy or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl;

each R⁷ is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, CO₂H, CONH₂, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl, C₃-C₆ trialkylsilyl; or

each R⁷ is independently a phenyl, benzyl, benzoyl, phenoxy or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl;

provided that when A and B are both O, R² is H or C₁-C₃ alkyl, R³ is H or C₁-C₃ alkyl and R⁴ is H, halogen, C₁-C₆ alkyl, phenyl, hydroxy or C₁-C₆ alkoxy, then one R⁵ is other than halogen, C₁-C₆ alkyl, hydroxy or C₁-C₆ alkoxy.

Also of note are methods for controlling arthropods comprising contacting the arthropods or their environment with an arthropodicidally effective amount of a compound of Formula IV and insecticidal compositions thereof.

Preferred methods for reasons of better activity are:

Preferred 1. Methods comprising compounds of Formula 1 wherein J is a phenyl group substituted with 1 to 2 R⁵ and optionally substituted with 1 to 3 R⁶.

Preferred 2. Methods of Preferred 1 wherein

A and B are both O;

n is 1 to 2;

R¹ is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl;

R² is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl;

R³ is C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆ cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, C₁-C₂ alkoxy, C₁-C₂ alkylthio, C₁-C₂ alkylsulfinyl and C₁-C₂ alkylsulfonyl;

one of the R⁴ groups is attached to the phenyl ring at the 2-position or 5-position, and said R⁴ is C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl or C₁-C₄ haloalkylsulfonyl;

each R⁵ is independently C₁-C₄ haloalkyl, CN, NO₂, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl or C₂-C₄ alkoxycarbonyl; or

(R⁵)₂ when attached to adjacent carbon atoms can be taken together as —OCF₂O—, —CF₂CF₂O— or —OCF₂CF₂O—; and

each R⁶ is independently H, halogen, C₁-C₄ alkyl, C₁-C₂ alkoxy or C₂-C₄ alkoxycarbonyl, or

each R⁶ is independently a phenyl or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl.

Preferred 3. Methods of Preferred 2 wherein

R¹ and R² are both H;

R³ is C₁-C₄ alkyl optionally substituted with halogen, CN, OCH₃, S(O)_(p)CH₃;

each R⁴ is independently H, CH₃, CF₃, OCF₃, OCHF₂, S(O)_(p)CF₃, S(O)_(p)CHF₂, CN or halogen;

each R⁵ is independently CF₃, OCF₃, OCHF₂, S(O)_(p)CF₃, S(O)_(p)CHF₂, OCH₂CF₃, OCF₂CHF₂, S(O)_(p)CH₂CF₃ or S(O)_(p)CF₂CHF₂;

each R⁶ is independently H, halogen or methyl; or phenyl, pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen or CN; and

p is 0, 1 or 2.

Preferred 4. Methods of Preferred 3 wherein R³ is i-propyl or t-butyl.

Preferred 5. Methods comprising compounds of Formula 1 wherein J is a 5- or 6-membered heteroaromatic ring optionally substituted with 1 to 4 R⁷.

Preferred 6. Methods of Preferred 5 wherein

J is a 5- or 6-membered heteroaromatic ring selected from the group consisting of J-1, J-2, J-3, J4 and J-5, each J optionally substituted with 1 to 3 R⁷

Q is O, S or NR⁷; and

W, X, Y and Z are independently N or CR⁷, provided that in J-4 and J-5 at least one of W, X, Y or Z is N.

Preferred 7. Methods of Preferred 5 or Preferred 6 wherein

A and B are O;

n is 1 to 2;

R¹ is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl;

R² is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl;

R³ is H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆ cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, C₁-C₂ alkoxy, C₁-C₂ alkylthio, C₁-C₂ alkylsulfinyl and C₁-C₂ alkylsulfonyl;

one of the R⁴ groups is attached to the phenyl ring at the 2-position, and said R⁴ is C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, or C₁-C₄ haloalkylsulfonyl; and

each R⁷ is independently H, C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen, CN, NO₂, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl or C₂-C₄ alkoxycarbonyl; or a phenyl or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl.

Preferred 8. Methods of Preferred 7 wherein

J is selected from the group consisting of pyridine, pyrimidine, pyrazole, imidazole, triazole, thiophene, thiazole and oxazole, furan, isothiazole and isoxazole, each optionally substituted with 1 to 3 R⁷.

Preferred 9. Methods of Preferred 8 wherein

J is selected from the group consisting of pyridine, pyrimidine, pyrazole, thiophene and thiazole, each optionally substituted with 1 to 3 R⁷;

R¹ and R² are both H;

R³ is C₁-C₄ alkyl optionally substituted with halogen, CN, OCH₃, S(O)_(p)CH₃;

each R⁴ is independently H, CH₃, CF₃, OCF₃, OCHF₂, S(O)_(p)CF₃, S(O)_(p)CHF₂, CN or halogen;

each R⁷ is independently H, halogen, CH₃, CF₃, OCHF₂, S(O)_(p)CF₃, S(O)_(p)CHF₂, OCH₂CF₃, OCF₂CHF₂, S(O)_(p)CH₂CF₃, S(O)_(p)CF₂CHF₂; or phenyl, pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, halogen or CN; and

p is 0, 1 or 2.

Preferred 10. Methods of Preferred 9 wherein J is a pyridine optionally substituted with 1 to 3 R⁷.

Preferred 11. Methods of Preferred 10 wherein one R⁷ is a phenyl optionally substituted with C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen or CN.

Preferred 12. Methods of Preferred 10 wherein one R⁷ is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with C₁C₄ alkyl, C₁-C₄ haloalkyl, halogen or CN.

Preferred 13. Methods of Preferred 9 wherein J is a pyrimidine optionally substituted with 1 to 3 R⁷.

Preferred 14. Methods of Preferred 13 wherein one R⁷ is a phenyl optionally substituted with C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen or CN.

Preferred 15. Methods of Preferred 13 wherein one R⁷ is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen or CN.

Preferred 16. Methods of Preferred 9 wherein J is a pyrazole optionally substituted with 1 to 3 R⁷.

Preferred 17. Methods of Preferred 16 wherein one R⁷ is a phenyl optionally substituted with C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen or CN.

Preferred 18. Methods of Preferred 16 wherein one R⁷ is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen or CN.

Preferred 19. Methods of Preferred 18 wherein R⁷ is a pyridine optionally substituted with C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen or CN.

Most preferred is the method comprising a compound of Formula 1 selected from the group consisting of:

3-methyl-N-(1-methylethyl)-2-[[4-(trifluoromethyl)benzoyl]amino]-benzamide,

2-methyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-4-(trifluoromethyl)benzamide,

2-methyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-6-(trifluoromethyl)-3-pyridinecarboxamide,

1-ethyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide,

1-(2-fluorophenyl)-N-[2-methyl-6-[[(1-methylethyl)amino)carbonyl]phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide,

1-(3-chloro-2-pyridinyl)-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]3-(trifluoromethyl)-1H-pyrazole-5-carboxamide,

N-[2-chloro-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide,

3-bromo-1-(2-chlorophenyl)-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1H-pyrazole-5-carboxamide, and

3-bromo-N-[2-chloro-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1-(2-chlorophenyl)-1H-pyrazole-5-carboxamide.

Preferred compounds for reasons of better activity and/or ease of synthesis are:

Preferred A. Compounds of Formula 1 wherein J is a phenyl group substituted with 1 to 2 R⁵ and optionally substituted with 1 to 3 R⁶.

Preferred B. Compounds of Preferred A wherein

A and B are both O;

n is 1 to 2;

R¹ is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl;

R² is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl;

R³ is C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆ cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, C₁-C₂ alkoxy, C₁-C₂ alkylthio, C₁-C₂ alkylsulfinyl and C₁-C₂ alkylsulfonyl;

one of the R⁴ groups is attached to the phenyl ring at the 2-position or 5-position, and said R⁴ is C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl or C₁-C₄ haloalkylsulfonyl;

each R⁵ is independently C₁-C₄ haloalkyl, CN, NO₂, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl or C₂-C₄ alkoxycarbonyl; or

(R⁵)₂ when attached to adjacent carbon atoms can be taken together as —OCF₂O—, —CF₂CF₂O— or —OCF₂CF₂O—; and

each R⁶ is independently H, halogen, C₁-C₄ alkyl, C₁-C₂ alkoxy or C₂-C₄ alkoxycarbonyl, or

each R⁶ is independently a phenyl or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl.

Preferred C. Compounds of Preferred B wherein

R¹ and R² are both H;

R³ is C₁-C₄ alkyl optionally substituted with halogen, CN, OCH₃, S(O)_(p)CH₃;

each R⁴ is independently H, CH₃, CF₃, OCF₃, OCHF₂, S(O)_(p)CF₃, S(O)_(p)CHF₂, CN or halogen;

each R⁵ is independently CF₃, OCF₃, OCHF₂, S(O)_(p)CF₃, S(O)_(p)CHF₂, OCH₂CF₃, OCF₂CHF₂, S(O)_(p)CH₂CF₃ or S(O)_(p)CF₂CHF₂;

each R⁶ is independently H, halogen or methyl; or phenyl, pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen or CN; and

p is 0, 1 or 2.

Preferred D. Compounds of Preferred C wherein R³ is i-propyl or t-butyl.

Preferred E. Compounds of Formula 1 wherein J is a 5- or 6-membered heteroaromatic ring optionally substituted with 1 to 4 R⁷.

Preferred F. Compounds of Preferred E wherein

J is a 5- or 6-membered heteroaromatic ring selected from the group consisting of J-1, J-2, J-3, J-4 and J-5, each J optionally substituted with 1 to 3 R⁷

Q is O, S or NR⁷; and

W, X, Y and Z are independently N or CR⁷, provided that in J-4 and J-5 at least one of W, X, Y or Z is N.

Preferred G. Compounds of Preferred E or Preferred F wherein

A and B are O;

n is 1 to 2;

R¹ is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl;

R² is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl;

R³ is H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆ cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, C₁-C₂ alkoxy, C₁-C₂ alkylthio, C₁-C₂ alkylsulfinyl and C₁-C₂ alkylsulfonyl;

one of the R⁴ groups is attached to the phenyl ring at the 2-position, and said R⁴ is C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl or C₁-C₄ haloalkylsulfonyl; and

each R⁷ is independently H, C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen, CN, NO₂, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl or C₂-C₄ alkoxycarbonyl; or a phenyl or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl.

Preferred H. Compounds of Preferred G wherein

J is selected from the group consisting of pyridine, pyrimidine, pyrazole, imidazole, triazole, thiophene, thiazole and oxazole, furan, isothiazole and isoxazole, each optionally substituted with 1 to 3 R⁷.

Preferred I. Compounds of Preferred H wherein

J is selected from the group consisting of pyridine, pyrimidine, pyrazole, thiophene and thiazole, each optionally substituted with 1 to 3 R⁷;

R¹ and R² are both H;

R³ is C₁-C₄ alkyl optionally substituted with halogen, CN, OCH₃, S(O)_(p)CH₃;

each R⁴ is independently H, CH₃, CF₃, OCF₃, CHF₂, S(O)_(p)CF₃, S(O)_(p)CHF₂, CN or halogen;

each R⁷ is independently H, halogen, CH₃, CF₃, OCHF₂, S(O)_(p)CF₃, S(O)_(p)CHF₂, OCH₂CF₃, OCF₂CHF₂, S(O)_(p)CH₂CF₃, S(O)_(p)CF₂CHF₂; or phenyl, pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, halogen or CN; and

p is 0, 1 or 2.

Preferred J. Compounds of Preferred I wherein J is a pyridine optionally substituted with 1 to 3 R⁷.

Preferred K. Compounds of Preferred J wherein one R⁷ is a phenyl optionally substituted with C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen or CN.

Preferred L. Compounds of Preferred J wherein one R⁷ is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen or CN.

Preferred M. Compounds of Preferred I wherein J is a pyrimidine optionally substituted with 1 to 3 R⁷.

Preferred N. Compounds of Preferred M wherein one R⁷ is a phenyl optionally substituted with C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen or CN.

Preferred O. Compounds of Preferred M wherein one R⁷ is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen or CN.

Preferred P. Compounds of Preferred I wherein J is a pyrazole optionally substituted with 1 to 3 R⁷.

Preferred Q. Compounds of Preferred P wherein one R⁷ is a phenyl optionally substituted with C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen or CN.

Preferred R. Compounds of Preferred P wherein one R⁷ is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen or CN.

Preferred S. Compounds of Preferred R wherein R⁷ is a pyridine optionally substituted with C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen or CN.

Most preferred is the compound of Formula 1 selected from the group consisting of:

3-methyl-N-(1-methylethyl)-2-[[4-(trifluoromethyl)benzoyl]amino]-benzamide,

2-methyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-4-(trifluoromethyl)benzamide,

2-methyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-6-(trifluoromethyl)-3-pyridinecarboxamide,

1-ethyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide,

1-(2-fluorophenyl)-N-[2-methyl-6-[[(1-methylethyl)amino)carbonyl]phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide,

1-(3-chloro-2-pyridinyl)-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]3-(trifluoromethyl)-1H-pyrazole-5-carboxamide,

N-[2-chloro-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide,

3-bromo-1-(2-chlorophenyl)-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1H-pyrazole-5-carboxamide, and

3-bromo-N-[2-chloro-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1-(2-chlorophenyl)-1H-pyrazole-5-carboxamide.

Preferred compositions are those comprising compounds of formula 1 as preferred in Preferred 1 through 19, and the specifically preferred compounds above.

As noted above, each J is independently a phenyl group or a naphthyl group substituted with 1 to 2 R⁵ and optionally substituted with 1 to 3 R⁶; or each J is independently a 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system wherein each ring or ring system is optionally substituted with 1 to 4 R⁷. The term “optionally substituted” in connection with these J groups refers to groups which are unsubstituted or have at least one non-hydrogen substituent that does not extinguish the arthropodicidal activity possessed by the unsubstituted analog. Note also that J-1 through J-5 above denote 5- or 6-membered heteroaromatic rings. An example of phenyl substituted with 1 to 2 R⁵ and optionally substituted with 1 to 3 R⁶ is the ring illustrated as J-6 in Exhibit 1, wherein m is an integer from 1-2 and q is an integer from 1 to 3. Note that at least one R⁵ must be present in J-6. Although R⁶ groups are shown in the structure J-6, it is noted that they do not need to be present since they are optional substituents. An example of a naphthyl group substituted with 1 to 2 R⁵ and optionally substituted with 1 to 3 R⁶ is J-59 illustrated in Exhibit 1, wherein m is an integer from 1-2 and q is an integer from 1 to 3. Note that at least one R⁵ must be present in J-59. Although R⁶ groups are shown in the structure J-59, it is noted that they do not need to be present since they are optional substituents. Examples of 5- or 6-membered heteroaromatic ring optionally substituted with 1 to 4 R⁷ include the rings J-7 through J-58 illustrated in Exhibit 1 wherein r is an integer from 1 to 4. Note that J-7 through J-26 are examples of J-1, J-27 through J-41 are examples of J-2, J-42 through J-44 are examples of J-3, J-46 through J-53 are examples of J-4 and J-54 through J-58 are examples of J-5. The nitrogen atoms that require substitution to fill their valence are substituted with R⁷. Note that some J groups can only be substituted with less than 4 R⁷ groups (e.g. J-19, J-20, J-23 through J-26 and J-37 through J-40 can only be substituted with one R⁷). Examples of aromatic 8-, 9- or 10-membered fused heterobicyclic ring systems optionally substituted with 1 to 4 R⁷ include J-60 through J-90 illustrated in Exhibit 1 wherein r is an integer from 1 to 4. Although R⁷ groups are shown in the structures J-7 through J-58 and J-60 through J-90, it is noted that they do not need to be present since they are optional substituents. Note that when R⁵, R⁶ and/or R⁷ are H when attached to an atom, this is the same as if said atom is unsubstituted. Note that when the attachment point between (R⁵)_(m), (R⁶)_(q) or (R⁷)_(r) and the J group is illustrated as floating, (R⁵)_(m), (R⁶)_(q) or (R⁷)_(r) can be attached to any available carbon atom of the J group. Note that when the attachment point on the J group is illustrated as floating, the J group can be attached to the remainder of Formula 1 through any available carbon of the J group by replacement of a hydrogen atom.

As noted above, G is a 5- or 6-membered nonaromatic carbocyclic or heterocyclic ring, optionally including one or two ring members selected from the group consisting of C(═O), SO or S(O)₂ and optionally substituted with 1 to 4 substituents selected from the group consisting of C₁-C₂ alkyl, halogen, CN, NO₂ and C₁-C₂ alkoxy. The term “optionally substituted” in connection with these G groups refers to groups which are unsubstituted or have at least one non-hydrogen substituent that does not extinguish the arthropodicidal activity possessed by the unsubstituted analog. Note that when the attachment point on the G group is illustrated as floating, the G group can be attached to the remainder of Formula 1 through any available carbon of the G group by replacement of a hydrogen atom. The optional substituents can be attached to any available carbon by replacing a hydrogen atom. Examples of 5- or 6-membered nonaromatic carbocyclic rings as G include the rings illustrated as G-1 through G-8 of Exhibit 2, wherein such rings are optionally substituted with 1 to 4 substituents selected from the group consisting of C₁-C₂ alkyl, halogen, CN, NO₂ and C₁-C₂ alkoxy. Examples of 5- or 6-membered nonaromatic heterocyclic rings as G include the rings illustrated as G-9 through G-48 of Exhibit 2, wherein such rings are optionally substituted with 1 to 4 substituents selected from the group consisting of C₁-C₂ alkyl, halogen, CN, NO₂ and C₁-C₂ alkoxy. Note that when G comprises a ring selected from G-31 through G-34, G-37 and G-38, Q¹ is selected from O, S or N. Note that when G is G-11, G13, G-14, G16, G-23, G-24, G-30 through G-34, G-37 and G-38 and Q¹ is N, the nitrogen atom can complete its valence by substitution with either H or C₁-C₂ alkyl.

As noted above, each R⁶ and each R⁷ can be independently (among others) 5- or 6-membered heteroaromatic rings or aromatic 8-, 9- or 10-membered fused heterobicyclic ring systems, each ring optionally substituted with one to three substituents independently selected from the group consisting of C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl. Examples of such R⁶ and R⁷ groups include the rings or ring systems illustrated as rings J-7 through J-58 and J-60 through J-90 illustrated in Exhibit 1, except that such rings are optionally substituted with 1 to 3 substituents selected from the group consisting of C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl rather than (R⁷)_(r). Note that these substituents can be attached to any available carbon atom of the J group by replacement of a hydrogen atom. Note that when the attachment point on the J group is illustrated as floating, the J group can be attached to the remainder of Formula 1 through any available carbon of the J group by replacement of a hydrogen atom.

One or more of the following methods and variations as described in Schemes 1-17 can be used to prepare the compounds of Formula 1. The definitions of A, B, J, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, m and n in the compounds of Formulae 1-34 below are as defined above in the Summary of the Invention. Compounds of Formulae 1a-c, 2a-b, 4a-g, 5a-b are various subsets of the compounds of Formula 1, 2, 4 and 5.

Compounds of Formula 1 can be prepared by procedures outlined in Schemes 1-17. A typical procedure is detailed in Scheme 1 and involves coupling of an anthranilic amide of Formula 2 with an acid chloride of Formula 3 in the presence of an acid scavenger to provide the compound of Formula 1a. Typical acid scavengers include amine bases such as triethylamine, diisopropylethylamine and pyridine; other scavengers include hydroxides such as sodium and potassium hydroxide and carbonates such as sodium carbonate and potassium carbonate. In certain instances it is useful to use polymer-supported acid scavengers such as polymer-bound diisopropylethylamine and polymer-bound dimethylaminopyridine. In a subsequent step, amides of Formula 1a can be converted to thioamides of Formula 1b using a variety of standard thio transfer reagents including phosphorus pentasulfide and Lawesson's reagent.

An alternate procedure for the preparation of compounds of Formula 1a involves coupling of an anthranilic amide of Formula 2 with an acid of Formula 4 in the presence of a dehydrating agent such as dicyclohexylcarbodiimide (DCC). Polymer supported reagents are again useful here, such as polymer-bound cyclohexylcarbodiimide. Synthetic procedures of Schemes 1 and 2 are only representative examples of useful methods for the preparation of Formula 1 compounds as the synthetic literature is extensive for this type of reaction.

One skilled in the art will also realize that acid chlorides of Formula 3 may be prepared from acids of Formula 4 by numerous well-known methods.

Anthranilic amides of Formula 2a are typically available from the corresponding 2-nitrobenzamides of Formula 5 via catalytic hydrogenation of the nitro group. Typical procedures involve reduction with hydrogen in the presence of a metal catalyst such as palladium on carbon or platinum oxide and in hydroxylic solvents such as ethanol and isopropanol. These procedures are well documented in the chemical literature. R¹ substituents such as alkyl, substituted alkyl and the like can generally be introduced at this stage through known procedures including either direct alkylation or through the generally preferred method of reductive alkylation of the amine. A commonly employed procedure is to combine the aniline 2a with an aldehyde in the presence of a reducing agent such as sodium cyanoborohydride to produce the Formula 2b compounds where R¹ is alkyl, alkenyl, alkynyl or substituted derivatives thereof.

The intermediate amides of Formula 5a are readily prepared from commercially available 2-nitrobenzoic acids. Typical methods for amide formation can be applied here. These include direct dehydrative coupling of acids of Formula 6 with amines of Formula 7 using for example DCC, and conversion of the acids to an activated form such as the acid chlorides or anhydrides and subsequent coupling with amines to form amides of Formula 5a. We have found ethylchloroformate to be an especially useful reagent for this type of reaction involving activation of the acid. The chemical literature is extensive on this type of reaction. Amides of Formula 5a are readily converted to thioamides of Formula 5b by using commercially available thio transfer reagents such as phosphorus pentasulfide and Lawesson's reagent.

Benzoic acids of Formula 4 (J is optionally substituted phenyl) are generally well known in the art as are procedures for their preparation. One particularly useful subset of benzoic acids of this invention are 2-methyl-4-perfluoroalkyl benzoic acids of Formula 4a (R⁵ equals e.g. CF₃, C₂F₅, C₃F₇). The synthesis for these compounds is outlined in Schemes 5-9. Benzoic acids of Formula 4a may be prepared from the benzonitriles of Formula 8 by hydrolysis. The conditions used may involve the use of a base such as an alkaline metal hydroxide or alkoxide (e.g. potassium or sodium hydroxide) in a solvent such as water, ethanol or ethylene glycol (e.g. J. Chem. Soc. 1948, 1025). Alternatively, the hydrolysis may be carried out using an acid such as sulfuric acid or phosphoric acid in a suitable solvent such as water (e.g. Org. Synth. 1955, Coll vol. 3, 557). The choice of the conditions is contingent on the stability of R⁵ to the reaction conditions and elevated temperatures are usually employed to achieve this transformation.

Nitriles of Formula 8 may be prepared from anilines of Formula 9 by the classical sequence involving diazotization and treatment of the intermediate diazonium salt with a copper cyanide salt (e.g. J. Amer. Chem. Soc. 1902, 24, 1035).

Anilines of Formula 9 may be prepared from compounds of Formula 10. This transformation may be achieved by a well-known procedure that employs Raney Nickel (Org. Synth. Coll. Vol VI, 581). Alternatively, the same transformation may be effected by the use of a suitable catalyst such as palladium in the presence of hydrogen. The reaction is usually conducted at pressures of 10² to 10⁵ kPa in a suitable organic solvent such as, but not limited to, toluene. Elevated temperatures of 80-110° C. are usually required to achieve the transformation. As one skilled in the art will realize, numerous chemical modifications of the thioether moiety are possible, and may be employed when necessary to facilitate this transformation.

Compounds of Formula 10 may be prepared from iminosulfuranes of Formula 11. The transformation may be achieved in a protic solvent such as methanol or water, in a non-protic solvent such as dichloromethane or toluene in the presence of a suitable base such as triethylamine (e.g. Org. Synth. Coll. Vol. VI, 581) or sodium methoxide, or in a combination of a protic solvent, a non-protic solvent and a base. The temperature at which the reaction is conducted is usually in the range 40-110° C. As one skilled in the art will realize, suitable salts of compounds of Formula 11 such as, but not limited to a hydrochloride, a sulfate or a bisulfate may also be employed, provided that the appropriate amount of base is first used to generate the free base 11. This may be done as a separate step or as an integral part of the step involving the transformation of compounds of Formula 11 to compounds of Formula 10.

Compounds of Formula 11 may be prepared from anilines of Formula 12 by reaction with dimethyl sulfide and a suitable chlorinating agent such as, but not limited to N-chlorosuccinimide (e.g. Org. Synth Coll. Vol. VI, 581), chlorine or N-chlorobenzotriazole. Alternatively, anilines of Formula 12 may be treated with dimethyl sulfoxide which has been “activated” by treatment with an agent such as acetic anhydride, trifluoroacetic, anhydride, trifluoromethanesulfonic anhydride, cyclohexylcarbodiimide, sulfur trioxide, or phosphorus pentoxide. The reaction is conducted in a suitable organic solvent such as dichloromethane or dimethyl sulfoxide. The reaction is conducted at a temperature of −70° C. to 25° C. and is dependent on the solvent and reagent used.

Intermediate anthranilic amides of Formula 2a and 2b may also be prepared from isatoic anhydrides of Formula 13 and 14 (Scheme 10). Typical procedures involve combination of equimolar amounts of the amine 7 with the isatoic anhydride in polar aprotic solvents such as pyridine and dimethylformamide at temperatures ranging from room temperature to 100° C. R¹ substituents such as alkyl and substituted alkyl may be introduced by the base catalyzed alkylation of isatoic anhydride 13 with known alkylating reagents R¹-Lg (wherein Lg is a leaving group such as halogen, alkyl or aryl suphonates or alkyl sulfates) to provide the alkyl substituted intermediates 14. Isatoic anhydrides of Formula 13 may be made by methods described in Coppola, Synthesis 505-36 (1980).

An alternate procedure for the preparation of specific compounds of Formula 1 (where A is O, B is O and R¹ is H) involves reaction of an amine 7 with a benzoxazinone of Formula 15. Typical procedures involve combination of the amine with the benzoxazinone in solvents such as tetrahydrofuran or pyridine at temperatures ranging from room temperature to the reflux temperature of the solvent. Benzoxazinones are well documented in the chemical literature and are available via known methods that involve the coupling of either an anthranilic acid or an isatoic anhydride with an acid chloride. For references to the synthesis and chemistry of Benzoxazinones see Jakobsen et al, Biorganic and Medicinal Chemistry, 2000, 8, 2095-2103 and references cited within. See also Coppola, J. Heterocyclic Chemistry, 1999, 36, 563-588.

Heterocyclic acids 4, where J is equal to an optionally substituted heterocycle, can be prepared by procedures outlined in Schemes 12-17. Both general and specific references to a wide variety of heterocyclic acids including thiophenes, furans, pyridines, pyrimidines, triazoles, imidazoles, pyrazoles, thiazoles, oxazoles, isothiazoles, thiadiazoles, oxadiazoles, triazines, pyrazines, pyridazines, and isoxazoles can be found in the following compendia: Rodd's Chemistry of Chemistry of Carbon Compounds, Vol. IVa to IVI., S. Coffey editor, Elsevier Scientific Publishing, New York, 1973; Comprehensive Heterocyclic Chemistry, Vol. 1-7, A. R. Katritzky and C. W. Rees editors, Pergamon Press, New York, 1984; Comprehensive Heterocyclic Chemistry II, Vol. 1-9, A. R. Katritzky, C. W. Rees, and E. F. Scriven editors, Pergamon Press, New York, 1996; and the series, The Chemistry of Heterocyclic Compounds, E. C. Taylor, editor, Wiley, New York. Particularly useful heterocyclic acids of this invention include pyridine acids, pyrimidine acids and pyrazole acids. Procedures for the synthesis of representative examples of each are detailed in Schemes 12-17. A variety of heterocyclic acids and general methods for their synthesis may be found in World Patent Application WO 98/57397.

The synthesis of representative pyridine acids (4b) is depicted in Scheme 12. This procedure involves the known synthesis of pyridines from β-ketoesters and 4-aminobutenones (19). Substituent groups R⁷(a) and R⁷(b) include e.g. alkyl and haloalkyl.

The synthesis of representative pyrimidine acids (4c) is depicted in Scheme 13. This procedure involves the known synthesis of pyrimidines from vinylidene-β-ketoesters (22) and amidines. Substituent groups R⁷(a) and R⁷(b) include e.g. alkyl and haloalkyl.

The synthesis of representative pyrazole acids (4d-4g) is depicted in Schemes 14-17. Pyrazoles 4d are described in Scheme 14. The synthesis of Scheme 14 involves as the key step introduction of the R⁷(b) substituent via alkylation of the pyrazole. The alkylating agent R⁷(b)-Lg (wherein Lg is a leaving group such as Cl, Br, I, sulfonates such as p-toluenesulfonate or methanesulfonate or sulfates such as —SO₂OR⁷(b)) includes R⁷(b) groups such as C₁-C₆ alkyl, C₂C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₃-C₈ dialkylaminocarbonyl, C₃-C₆ trialkylsilyl; or phenyl, benzyl, benzoyl, 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, each ring or ring system optionally substituted. Oxidation of the methyl group affords the pyrazole carboxylic acid. Some of the more preferred R⁷(a) groups include haloalkyl.

Pyrazoles 4e are described in Scheme 15. These pyrazole acids may be prepared via metallation and carboxylation of pyrazoles of formula 28 as the key step. The R⁷(b) group is introduced in a manner similar to that of Scheme 14, i.e. via alkylation with a R⁷(b) alkylating agent. Representative R⁷(a) groups include e.g. cyano, and haloalkyl.

Pyrazoles 4f are described in Scheme 16. These can be prepared via reaction of an optionally substituted phenyl hydrazine 29 with a pyruvate 30 to yield pyrazole esters 31. Hydrolysis of the ester affords the pyrazole acids 4f. This procedure is particularly useful for the preparation of compounds where R⁷(b) is optionally substituted phenyl and R⁷(a) is haloalkyl.

Pyrazoles acids of Formula 4g are described in Scheme 17. These can be prepared via 3+2 cycloaddition of an appropriately substituted nitrilimine with either substituted propiolates (33) or acrylates (36). Cycloaddition with acrylates requires additional oxidation of the intermediate pyrazoline to the pyrazole. Hydrolysis of the ester affords the pyrazole acids 4g. Preferred iminohalides for this reaction include the trifluoromethyl iminochloride (38) and the iminodibromide (39). Compounds such as 38 are known (J. Heterocycl. Chem. 1985, 22(2), 565-8). Compounds such as 39 are available by known methods (Tetrahedron Letters 1999, 40, 2605). These procedures are particularly useful for the preparation of compounds where R⁷(b) is optionally substituted phenyl and R⁷(a) is haloalkyl or bromo.

It is recognized that some reagents and reaction conditions described above for preparing compounds of Formula 1 may not be compatible with certain functionalities present in the intermediates. In these instances, the incorporation of protection/deprotection sequences or functional group interconversions into the synthesis will aid in obtaining the desired products. The use and choice of the protecting groups will be apparent to one skilled in chemical synthesis (see, for example, Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991). One skilled in the art will recognize that, in some cases, after the introduction of a given reagent as it is depicted in any individual scheme, it may be necessary to perform additional routine synthetic steps not described in detail to complete the synthesis of compounds of Formula 1. One skilled in the art will also recognize that it may be necessary to perform a combination of the steps illustrated in the above schemes in an order other than that implied by the particular sequence presented to prepare the compounds of Formula 1.

One skilled in the art will also recognize that compounds of Formula 1 and the intermediates described herein can be subjected to various electrophilic, nucleophilic, radical, organometallic, oxidation, and reduction reactions to add substituents or modify existing substituents.

Without further elaboration, it is believed that one skilled in the art using the preceding description can utilize the present invention to its fullest extent. The following Examples are, therefore, to be construed as merely illustrative, and not limiting of the disclosure in any way whatsoever. Percentages are by weight except for chromatographic solvent mixtures or where otherwise indicated. Parts and percentages for chromatographic solvent mixtures are by volume unless otherwise indicated. ¹H NMR spectra are reported in ppm downfield from tetramethylsilane; s is singlet, d is doublet, t is triplet, q is quartet, m is multiplet, dd is doublet of doublets, dt is doublet of triplets, br s is broad singlet.

EXAMPLE 1

Step A: Preparation of 3-methyl-N-(1-methylethyl)-2-nitrobenzamide

A solution of 3-methyl-2-nitrobenzoic acid (2.00 g, 11.0 mmol) and triethylamine (1.22 g, 12.1 mmol) in 25 mL of methylene chloride was cooled to 10° C. Ethyl chloroformate was carefully added and a solid precipitate formed. After stirring for 30 minutes isopropylamine (0.94 g, 16.0 mmol) was added and a homogeneous solution resulted. The reaction was stirred for an additional hour, poured into water and extracted with ethyl acetate. The organic extracts were washed with water, dried over magnesium sulfate and evaporated under reduced pressure to afford 1.96 g of the desired intermediate as a white solid melting at 126-128° C.

¹H NMR (CDCl₃) δ 1.24 (d,6H), 2.38 (s,3H), 4.22 (m,1H), 5.80 (br s,1H), 7.4 (m,3H).

Step B: Preparation of 2-amino-3-methyl-N-(1-methylethyl)benzamide

The 2-nitrobenzamide of Step A (1.70 g, 7.6 mmol) was hydrogenated over 5% Pd/C in 40 mL of ethanol at 50 psi. When the uptake of hydrogen ceased the reaction was filtered through celite and the celite was washed with ether. The filtrate was evaporated under reduced pressure to afford 1.41 g of the title compound as a solid melting at 149-151° C.

¹H NMR (CDCl₃) δ 1.24 (dd,6H), 2.16 (s,3H), 4.25 (m,1H), 5.54 (br s,2H), 5.85 (br s,1H), 6.59 (t,1H), 7.13 (d,1H), 7.17 (d,1H).

Step C: Preparation of 3-methyl-N-(1-methylethyl)-2-[[4-(trifluoromethoxy)benzoyl]amino]benzamide

4-(trifluoromethoxy)benzoyl chloride (0.29 g, 1.3 mmol) was added dropwise to a mixture of the aniline from Step B (0.25 g, 1.3 mmol) and triethylamine (0.13 g, 1.3 mmol) in 5 mL of methylene chloride at room temperature. After stirring for one hour the reaction was poured into water and extracted with ethyl acetate. The combined extracts were dried over magnesium sulfate and evaporated under reduced pressure. The resulting solids were washed with hexane/ether and filtered to afford 0.41 g of the title compound, a compound of the present invention, as a solid melting at 207-209° C.

¹H NMR (CDCl₃) δ 1.19 (d, 6H), 2.33 (s, 3H), 4.15 (m, 1H), 5.97 (br d, 1H), 7.2-7.4 (m, 6H), 8.04 (d, 1H), 10.11 (br s, 1H).

EXAMPLE 2

Step A: Preparation of 1-Ethyl-3-trifluoromethylpyrazol-5-yl Carboxylic acid

To a mixture of 3-trifluoromethylpyrazole (5 g, 37 mmol) and powdered potassium carbonate (10 g, 72 mmol) stirring in 30 mL of N,N-dimethylformamide, iodoethane (8 g, 51 mmol) was added dropwise. After a mild exotherm, the reaction was stirred overnight at room temperature. The reaction mixture was partitioned between 100 mL of diethyl ether and 100 mL of water. The ether layer was separated, washed with water (3×) and brine, and dried over magnesium sulfate. Evaporation of solvent in vacuo gave 4 g of oil.

To 3.8 g of this oil stirring in 40 mL of tetrahydrofuran under nitrogen in a dry ice/acetone bath, 17 mL of a 2.5 M solution of n-butyl lithium in tetrahydrofuran (43 mmol) was added dropwise and the solution stirred for 20 minutes at −78° C. An excess of gaseous carbon dioxide was bubbled into the stirred solution at a moderate rate for 10 minutes. After addition of carbon dioxide, the reaction was allowed to slowly reach room temperature and stirred overnight. The reaction mixture was partitioned between diethyl ether (100 mL) and 0.5 N aqueous sodium hydroxide (100 mL). The basic layer was separated and acidified with concentrated hydrochloric acid to a pH of 2-3. The aqueous mixture was extracted with ethyl acetate (100 mL) and the organic extract washed with water and brine and dried over magnesium sulfate. The oily residue, which remained after evaporating the solvent in vacuo, was triturated to a solid from a small amount of n-butyl chloride. After filtering and drying, a slightly impure, sample of 1-ethyl-3-trifluoromethyl-pyrazol-5-yl carboxylic acid (1.4 g) was obtained as a broad-melting solid.

¹H NMR (CDCl₃): 9.85 (br s,1H), 7.23 (s,1H), 4.68 (q,2H), 1.51 (t,3H) ppm.

Step B: Preparation of 2-[1-Ethyl-3-trifluoromethylpyrazol-5-yl carbamoyl]-3-methyl-N-(1-methylethyl)benzamide

To a solution of 1-ethyl-3-trifluoromethyl-pyrazol-5-yl carboxylic acid (0.5 g, 2.4 mmol) stirring in 20 mL of methylene chloride, oxalyl chloride (1.2 mL, 14 mmol) was added. Upon addition of 2 drops of N,N-dimethylformamide, foaming and bubbling occurred. The reaction mixture was heated at reflux for 1 hr as a yellow solution. After cooling, the solvent was removed in vacuo and the resulting residue dissolved in 20 mL of tetrahydrofuran. To the stirred solution, 2-amino-3-methyl-N-(1-methylethyl)benzamide (0.7 g, 3.6 mmol) was added followed by the dropwise addition of N,N-diisopropylethylamine (3 mL, 17 mmol). After stirring at room temperature overnight, the reaction mixture was partitioned between ethyl acetate (100 mL) and 1N aqueous hydrochloric acid (75 mL). The separated organic layer was washed with water and brine and dried over magnesium sulfate. Evaporating in vacuo gave a white solid residue, which on purification by flash column chromatography on silica gel (2:1 hexanes/ethyl acetate) afforded 0.5 g of the title compound, a compound of the present invention, melting at 223-226° C.

¹H NMR (DMSO-D₆): 10.15 (s,1H), 8.05 (d,1H), 7.45 (s,1H), 7.43-7.25 (m,3H), 4.58 (q,2H), 3.97 (m,1H), 2.45 (s,3H), 1.36 (t,3H), 1.06 (d,6H) ppm.

EXAMPLE 3

Step A: Preparation of S,S-dimethyl-N-[4-(trifluoromethyl)phenyl]sulfilimine

A solution of N-chlorosuccinimide (12-43 g, 93.1 mmol) in ˜170 mL of dichloromethane was added to a mixture of 4-(trifluoromethyl) aniline (15 g, 93.1 mmol) and dimethyl sulfide (6.35 g, 102 mmol) in 230 mL of dichloromethane at −5-0° C. After the addition was complete, the mixture was stirred at 0-5° C. for 1 h, and N-chlorosuccinimide (0.02 g, 4.64 mmol) was added. After a further 30 minutes, the mixture was washed with 500 mL of 1N sodium hydroxide.

The organic phase was dried and evaporated to give the product as a solid 19-72 g melting at 101-103° C. (after crystallization from ethyl acetate/hexanes).

IR (Nujol) 1603, 1562, 1532, 1502, 1428, 1402, 1335, 1300, 1270, 1185, 1150, 1103, 1067, 1000, 972, 940, 906, 837, 817 cm⁻¹.

¹H NMR (CDCl₃) δ 7.35 (d, J=8.8 Hz, 2 H), 6.84 (d, J=8.8 Hz, 2 H), 2.67 (5, 3 H).

Step B: 2-[(methylthio)methyl]-4-(trifluoromethyl)benzenamine

Sodium methoxide in methanol (1.95 g, 9.02 mmol, 25%) was added to S,S-dimethyl-N-[4-(trifluoromethyl)phenyl]sulfilimine from Step A (2 g, 9.04 mmol) in 15 mL of toluene. The mixture was warmed to ˜80° C. for ˜1 h. The mixture was allowed to cool to 25° C. and was poured into 100 mL of water. The mixture was extracted with 2×100 mL of ethyl acetate and the combined extracts were dried and evaporated to give 1.8 g of the product as a solid melting at 65.5-67.5° C. (after crystallization from hexanes).

IR (nujol) 3419, 3333, 1629, 1584, 1512, 1440, 1334, 1302, 1235, 1193, 1139, 1098, 1078, 979, 904, 832 cm⁻¹.

¹H NMR (CDCl₃) δ 7.35 (dd, J=1.5 Hz×8.2 Hz, 1H) 6.72 (d, J=8.4 Hz) 4.39 (br.5, 2 H, 3.69 (5, 2 H), 1.99 (5, 3 H).

Step C: Preparation of 2-methyl-4-(trifluoromethyl)benzenamine

Activated Raney nickel (500 g wet paste, ˜50μ) was added portionwise to a solution of 2-[(methylthio)methyl]-4-(trifluoromethyl)benzenamine (55.3 g, 0.25 mole) in 1 L of ethanol over 30 minutes at 25-30° C. The heterogeneous mixture was stirred vigorously for 30 minutes after the addition. The sting was stopped, and the solids were allowed to settle over one hour. The liquid was decanted from the solids and poured through filter paper. The filtrate was evaporated under reduced pressure, and the residue was taken up in dichloromethane. The organic phase was separated from a small volume of water, dried over magnesium sulfate and evaporated under reduced pressure to afford 37.6 g of the title compound as amber oil.

¹H NMR (CDCl₃) δ 7.28 (m,2H), 6.68 (d,1H), 3.87 (br s,2H), 2.19 (s,3H).

Step D: Preparation of 2-methyl-4-(trifluoromethyl)benzonitrile

Concentrated hydrochloric acid (16 mL) was added dropwise at a moderate rate to a heterogeneous mixture of 2-methyl-4-(trifluoromethyl)benzenamine (14 g, 80 mmol) and 120 mL of water while stirring vigorously. A thick suspension resulted which was stirred for 20 minutes, diluted with 280 mL of water and cooled to 5° C. A solution of sodium nitrite (5.5 g, 80 mmol) and 25 mL of water was added slowly to the reaction suspension. After stirring for 30 minutes at 5° C. a solution resulted which was stirred cold for 30 more minutes and then neutralized with potassium carbonate. This diazonium salt solution was then added portionwise via cannula to a stirred, 95° C. mixture of potassium cyanide (22 g, 0.34 mole), copper sulfate pentahydrate (20 g, 80 mmol) and 140 mL of water. After the addition the mixture was stirred for 30 minutes at 95° C. and then allowed to cool to room temperature. Ether was added and the heterogeneous mixture was filtered through celite. The solids were washed with ether, and the filtrate was partitioned. The aqueous phase was extracted with ether, and the combined organic extracts were dried over magnesium sulfate and concentrated under reduced pressure to afford 13.1 g of the title compound as brown oil.

¹H NMR (CDCl₃) δ 7.74 (d,1H), 7.60 (s,1H), 7.55 (d,1H), 2.64 (s,3H).

Step E: Preparation of 2-methyl-4-trifluoromethyl benzoic acid

Potassium hydroxide (15.7 g, 0.28 mole) and 15 mL of water were added as a solution to a stirred, heterogeneous mixture of 2-methyl-4-(trifluoromethyl)benzonitrile (13 g, 70 mmol) and 135 mL of ethylene glycol. The reaction mixture was heated at 120-130° C. for 20 hours and allowed to cool to room temperature. The dark solution was poured into 800 mL of water and filtered through celite. The filtrate was washed with ether and then the aqueous was acidified with concentrated hydrochloric acid. This aqueous phase was extracted three times with ethyl acetate, the organic extracts were combined, dried over magnesium sulfate and evaporated under reduced pressure to afford the title compound as a tan solid.

¹H NMR (CDCl₃) δ 7.98 (d,1H), 7.70 (s,1H), 7.65 (d,1H), 2.60 (s,3H).

Step F: Preparation of 2-methyl-4-(trifluoromethoxy)benzoyl chloride

Thionyl chloride (0.42 g, 3.5 mmol) was added to a solution of the benzoic acid from Step E (0.50 g, 2.4 mmol) in 10 mL of toluene at room temperature. The reaction was refluxed for three hours then cooled to room temperature. The solvent was evaporated under reduced pressure and excess thionyl chloride was removed by azeotroping with toluene. The benzoyl chloride obtained was used directly in Step G.

Step G: Preparation of 2-methyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-4-(trifluoromethyl)benzamide

The benzoyl chloride of Step F (0.29 g, 1.3 mmol) was added to a mixture of the aniline from Example 1, Step B (0.36 g, 1.9 mmol) and diisopropylethylamine (0.26 g, 2.0 mmol) in 10 mL of chloroform at room temperature. The reaction was allowed to stir overnight. The solid precipitate was filtered and dried to afford 0.38 g of the title compound, a compound of the present invention, as a solid melting at 247-248° C.

¹H NMR (CDCl₃) α 1.24 (d,6H), 2.41 (s,3H), 2.58 (s,3H), 4.20 (m,1H), 5.94 (br d,1H), 7.2-7.3 (m,2H), 7.40 (d,1H), 7.52 (s,1H), 7.53 (d,1H), 7.70 (d,1H), 9.36 (br s,1H).

EXAMPLE 4

Step A: Preparation of 2-Methyl-6-(trifluoromethyl)-3-pyridinecarbonyl chloride

Thionyl chloride (4.35 g, 36.5 mmol) was added to a mixture of 2-methyl-6-trifluoromethyl nicotinic acid (5.00 g, 24.4 mmol) in 75 mL of toluene and the mixture was heated at reflux for 3 hours. The reaction was cooled to room temperature and the solvent was removed under reduced pressure. Excess thionyl chloride was removed by azeotrope with toluene. The resultant acid chloride was used as is in Example 4, Step B.

Step B: Preparation of 8-Methyl-2-[2-methyl-6-(trifluoromethyl)-3-pyridinyl]-4H-3,1-benzoxazine

A mixture of the 6-methyl isatoic anhydride (3.92 g, 22.1 mmol) and the acid chloride from Step A (5.45 g, 24.3 mmol) was heated at reflux in pyridine for 16 hours. The dark brown solution was cooled to room temperature and the solvent was removed under reduced pressure. Excess pyridine was removed by azeotrope with toluene. Ether was added and the resulting brown solid was removed by filtration. The solid was taken up in a mixture of aqueous sodium bicarbonate and chloroform, the chloroform extracts were dried over magnesium sulfate and evaporated. Excess pyridine was again removed by azeotrope with toluene to afford 5.1 g of the title compound as a brown solid.

¹H NMR (CDCl₃) d 2.65 (s,3H), 3.11 (s,3H), 7.49 (t,1H) 7.40 (m,1H), 7.68-7.73 (m,2H), 1.11 (d,1H), 8.58 (d,1H).

Step C: Preparation of 2-Methyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-6-(trifluoromethyl)-3-pyridine

Isopropylamine (7.37 g, 0.125 mmol) was added to a mixture of the benzoxazinone of Step B (4.00 g, 12.5 mmol) in 30 mL of tetrahydrofuran. A homogeneous solution formed. The mixture was heated briefly after which a thick white precipitate formed. The solvent was removed under reduced pressure and the resultant solid was washed with ether and filtered to afford 4.48 g of the title compound as a solid melting at 247-248 C.

¹H NMR (CDCl₃) d 1.24 (d,6H), 2.41 (s,3H), 2.77 (s,3H), 4.17 (m,1H), 5.96 (bd,1H), 7.21 (m,2H) 7.40 (m,1H), 7.53 (d,1H), 7.97 (d,1H), 9.80 (bs,1H).

EXAMPLE 5

Step A: Preparation of 4-Methyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-2-(trifluoromethyl)-5-pyrimidinecarboxamide

To a solution 0.8 g (4 mmol) of 4-methyl-2-trifluoromethylpyrimidine-5-carboxylic acid [made by the method of Palanki et al, J. Med. Chem. 2000, 43, 3995] stirring in 15 mL of methylene chloride, oxalyl chloride (2 mL, 23 mmol) was added. Upon addition of 2 drops of N,N-dimethylformamide, foaming and bubbling occurred. The reaction mixture was heated at reflux for 1 hr as a yellow solution. After cooling, the solvent was removed in vacuo and the resulting residue dissolved in 20 mL of tetrahydrofuran. To the stirred solution, 2-amino-3-methyl-N-(1-methylethyl)benzamide (1 g, 5 mmol) was added followed by the dropwise addition of N,N-diisopropylethylamine (3 ml, 17 mmol). After stirring at room temperature overnight, the reaction mixture was partitioned between ethyl acetate (200 mL) and 1N aqueous hydrochloric acid (75 mL). The separated organic layer was washed with water and brine and dried over magnesium sulfate. Evaporating in vacuo gave a white solid, which was suspended in a small amount of ethyl acetate and filtered to afford (after drying) 650 mg of the title compound, a compound of the present invention, melting at 248-251° C.

¹H NMR (DMSO-D₆): 10.3 (s,NH), 9.07 (s,1H), 8.25 (d,NH), 7.43-7.25 (m,3H), 4.03 (m,1H), 2.73 (s,3H), 2.32 (s,3H), 1.12 (d,6H) ppm.

EXAMPLE 6

Step A: Preparation of 2-Methyl-1-phenyl-4-(trifluoromethyl)-1H-pyrazole

A solution of 1,1,1-trifluoropentane-2,4-dione (20.0 g, 0.130 mole) in glacial acetic acid (60 mL) was cooled to 7° C. using an ice/water bath. Phenylhydrazine (14.1 g, 0.130 mole) was added dropwise over a period of 60 minutes. The reaction mass temperature increased to 15° C. during the addition. The resulting orange solution was held under ambient conditions for 60 minutes. The bulk of the acetic acid was removed by stripping on a rotary evaporator at a bath temperature of 65° C. The residue was dissolved in methylene chloride (150 mL). The solution was washed with aqueous sodium bicarbonate (3 g in 50 mL water). The purple-red organic layer was separated, treated with activated charcoal (2 g) and MgSO₄, then filtered. Volatiles were removed on a rotary evaporator. The crude product consisted of 28.0 g of a rose-colored oil, which contained ˜89% the desired product and 11% 1-phenyl-5-(trifluoromethyl)-3-methylpyrazole.

¹H NMR (DMSO-D₆) δ 2.35 (s,3H), 6.76 (s,1H), 7.6-7.5 (m,5H).

Step B: Preparation of 1-Phenyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid

A sample of crude 1-phenyl-3-(trifluoromethyl)-5-methylpyrazole (˜89%, 50.0 g, 0.221 mole) was mixed with water (400 mL) and cetyltrimethylammonium chloride (4.00 g, 0.011 mole). The mixture was heated to 95° C. Potassium permanganate was added in 10 equal portions, spaced at ˜8 minute intervals. The reaction mass was maintained at 95-100° C. during this period. After the last portion was added, the mixture was held for ˜15 minutes at 95-100° C., whereupon the purple, permanganate color had been discharged. The reaction mass was filtered while hot (˜75° C.) through a 1 cm thick bed of Celite® on a 150 ml, coarse, glass frit. The filter cake was washed with warm (˜50° C.) water (3×100 mL). The combined filtrate and washings were extracted with ether (2×100 mL) to remove a small amount of yellow, water-insoluble material. The aqueous layer was purged with nitrogen to remove residual ether. The clear, colorless alkaline solution was acidified by adding concentrated hydrochloric acid dropwise until the pH reached ˜1.3 (28 g, 0.28 mole). Gas evolution was vigorous during the first two-thirds of the addition. The product was collected via filtration, washed with water (3×40 mL), then dried overnight at 55° C. in vacuo. The product consisted of 11.7 g of a white, crystalline powder, which was essentially pure based upon ¹H NMR.

¹H NMR (CDCl₃) δ 7.33 (s,1H), 7.4-7.5 (m,5H).

Step C: Preparation of 1-Phenyl-3-(trifluoromethyl)-1H-pyrazole-5-carbonyl chloride

A sample of crude 1-phenyl-3-(trifluoromethyl)pyrazole-5-carboxylic acid (4.13 g, 16.1 mmol) was dissolved in methylene chloride (45 mL). The solution was treated with oxalyl chloride (1.80 mL, 20.6 mmol), followed by N,N-dimethylformamide (0.010 mL, 0.13 mmol). Off-gassing began shortly after adding the N,N-dimethylformamide catalyst. The reaction mixture was stirred for ˜20 minutes under ambient conditions, then was heated to reflux for a period of 35 minutes. Volatiles were removed by stripping the reaction mixture on a rotary evaporator at a bath temperature of 55° C. The product consisted of 4.43 g of a light-yellow oil. The only impurity observed by ¹H NMR was N,N-dimethylformamide.

¹H NMR (CDCl₃) δ 7.40 (m,1H), 7.42 (s,1H), 7.50-7.53 (m,4H).

Step D: Preparation of N-[2-Methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1-phenyl-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide

A sample of 3-methylisatoic anhydride (0.30 g, 1.7 mmol) partially dissolved in pyridine (4.0 mL) was treated with 1-phenyl-3-(trifluoromethylpyrazole)-5-carboxyl chloride (0.55 g, 1.9 mmol). The mixture was heated to ˜95° C. for a period of 2 hours. The resulting orange solution was cooled to 29° C., then was treated with isopropylamine (1.00 g, 16.9 mmol). The reaction mass self-heated to 39° C. It was further heated to 55° C. for a period of 30 minutes, whereupon much precipitate formed. The reaction mass was dissolved in methylene chloride (150 mL). The solution was washed with aqueous acid (5 mL conc. HCl in 45 mL water), then with aqueous base (2 g sodium carbonate in 50 mL water). The organic layer was dried over MgSO₄, filtered, then concentrated on a rotary evaporator. Upon reduction to ˜4 mL, product crystals had formed. The slurry was diluted with ˜10 mL of ether, whereupon more product precipitated. The product was isolated by filtration, washed with ether (2×10 mL), then washed with water (2×50 mL). The wet cake was dried for 30 minutes at 70° C. in vacuo. The product consisted of 0.52 g of an off-white powder melting at 260-262° C.

¹H NMR (DMSO-D₆) δ 1.07 (d,6H), 2.21 (s,3H), 4.02 (octet,1H), 7.2-7.4 (m,3H), 7.45-7.6 (m,6H), 8.10 (d,1H), 10.31 (s,1H).

EXAMPLE 7

Step A: Preparation of 3-Trifluoromethyl-2-[3-(trifluoromethyl)-1H-pyrazol-1-yl]pyridine

A mixture of 2-chloro-3-trifluoromethylpyridine (3.62 g., 21 mmol), 3-trifluoromethylpyrazole (2.7 g., 20 mmol ), and potassium carbonate (6.0 g., 43 mmol) were heated at 100° C. for 18 h. The cooled reaction mixture was added to ice/water (100 mL). The mixture was extracted twice with ether (100 mL) and the combined ether extracts were washed twice with water (100 mL). The organic layer was dried with magnesium sulfate and concentrated to an oil. Chromatography on silica gel with hexanes:ethyl acetate 8:1 to 4:1 as eluent gave the title compound (3.5 g) as an oil. ¹H NMR (CDCl₃) δ 6.75 (m,1H), 7.5 (m,1H), 8.2 (m,2H), 8.7 (m,1H).

Step B: Preparation of 3-(Trifluoromethyl)-1-[3-(trifluoromethyl)-2-pyridinyl]-1H-pyrazole-5-carboxylic acid

A mixture of the title compound of Example 5, Step A (3.4 g, 13 mmol) was dissolved in tetrahydrofuran (30 mL) and cooled to −70° C. Lithium diisopropylamide (2N in heptane/tetrahydrofuran, (Aldrich) 9.5 mL, 19 mmol) was added and the resulting dark mixture was stirred for 10 minutes. Dry carbon dioxide was bubbled through the mixture for 15 minutes. The mixture was allowed to warm to 23° C. and treated with water (50 mL) and 1 N sodium hydroxide (10 mL). The aqueous mixture was extracted with ether (100 mL) and then ethyl acetate (100 mL). The aqueous layer was acidified with 6N hydrochloric acid to pH 1-2 and extracted twice with dichloromethane. The organic layer was dried with magnesium sulfate and concentrated to give the title compound (1.5 g). ¹H NMR (CDCl₃) δ 7.6 (m,1H), 7.95 (m,1H), 8.56 (m,1H), 8.9 (m,1H), 14.2 (br,1H)

Step C: Preparation of N-[2-Methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3-(trifluoromethyl)-1-[3-(trifluoromethyl)-2-pyridinyl]-1H-pyrazole-5-carboxamide

A mixture of the title compound of Example 5, Step B (0.54 g, 1.1 mmol), the title compound from Example 1, Step B (0.44 g, 2.4 mmol) and bop chloride (bis(2-oxo-oxazolidinyl)phosphinyl chloride, 0.54 g, 2.1 mmol) in acetonitrile (13 mL) was treated with triethylamine (0.9 mL). The mixture was shaken in a closed scintillation vial for 18 h. The reaction was partitioned between ethyl acetate (100 mL) and 1N hydrochloric acid. The ethyl acetate layer was washed successively with 1N hydrochloric acid (50 mL), 1N sodium hydroxide (50 mL) and saturated sodium chloride solution (50 mL). The organic layer was dried over magnesium sulfate and concentrated. The residue was subjected to column chromatography on silica gel with hexanes/ethyl acetate (5:1 to 3:1) as eluent. The title compound (0.43 g) was isolated as a white solid. m.p. 227-230° C. ¹H NMR (CDCl₃) δ 1.2 (m, 6H), 4.15 (m, 1H), 5.9 (br d,1H), 7.1 (m,1H), 7.2 (m,2H), 7.4 (s,1H), 7.6 (m,1H), 8.15 (m,1H), 8.74 (m,1H), 10.4 (br,1H).

By the procedures described herein together with methods known in the art, the following compounds of Tables 1 to 17 can be prepared. The following abbreviations are used in the Tables: t is tertiary, s is secondary, n is normal, i is iso, c is cyclo, Me is methyl, Et is ethyl, Pr is propyl, i-Pr is isopropyl, t-Bu is tert butyl, Ph is phenyl, OMe is methoxy, OEt is ethoxy, SMe is methylthio, SEt is ethylthio, CN is cyano, NO₂ is nitro, TMS is trimethylsilyl, S(O)Me is methylsulfinyl, and S(O)₂Me is methylsulfonyl.

TABLE 1

R⁴ R⁵ and/or R⁶ R⁴ R⁵ and/or R⁶ R⁴ R⁵ and/or R⁶ Me 2-CF₃ Me 3-CF₃ Me 4-CF₃ Me 2-OCF₃ Me 3-OCF₃ Me 4-OCF₃ Me 2-OCF₂H Me 3-OCF₂H Me 4-OCF₂H Me 2-OCF₂CF₂H Me 3-OCF₂CF₂H Me 4-OCF₂CF₂H Me 2-OCH₂CF₃ Me 3-OCH₂CF₃ Me 4-OCH₂CF₃ Me 2-SCF₃ Me 3-SCF₃ Me 4-SCF₃ Me 2-SOCF₃ Me 3-SOCF₃ Me 4-SOCF₃ Me 2-SO₂CF₃ Me 3-SO₂CF₃ Me 4-SO₂CF₃ Me 2-SCF₂H Me 3-SCF₂H Me 4-SCF₂H Me 2-SOCF₂H Me 3-SOCF₂H Me 4-SOCF₂H Me 2-SO₂CF₂H Me 3-SO₂CF₂H Me 4-SO₂CF₂H Cl 2-CF₃ Cl 3-CF₃ Cl 4-CF₃ Cl 2-OCF₃ Cl 3-OCF₃ Cl 4-OCF₃ Cl 2-OCF₂H Cl 3-OCF₂H Cl 4-OCF₂H Cl 2-OCF₂CF₂H Cl 3-OCF₂CF₂H Cl 4-OCF₂CF₂H Cl 2-OCH₂CF₃ Cl 3-OCH₂CF₃ Cl 4-OCH₂CF₃ Cl 2-SCF₃ Cl 3-SCF₃ Cl 4-SCF₃ Cl 2-SOCF₃ Cl 3-SOCF₃ Cl 4-SOCF₃ Cl 2-SO₂CF₃ Cl 3-SO₂CF₃ Cl 4-SO₂CF₃ Cl 2-SCF₂H Cl 3-SCF₂H Cl 4-SCF₂H Cl 2-SOCF₂H Cl 3-SOCF₂H Cl 4-SOCF₂H Cl 2-SO₂CF₂H Cl 3-SO₂CF₂H Cl 4-SO₂CF₂H F 2-CF₃ F 3-CF₃ F 4-CF₃ F 2-OCF₃ F 3-OCF₃ F 4-OCF₃ F 2-OCF₂H F 3-OCF₂H F 4-OCF₂H F 2-OCF₂CF₂H F 3-OCF₂CF₂H F 4-OCF₂CF₂H F 2-OCH₂CF₃ F 3-OCH₂CF₃ F 4-OCH₂CF₃ F 2-SCF₃ F 3-SCF₃ F 4-SCF₃ F 2-SOCF₃ F 3-SOCF₃ F 4-SOCF₃ F 2-SO₂CF₃ F 3-SO₂CF₃ F 4-SO₂CF₃ F 2-SCF₂H F 3-SCF₂H F 4-SCF₂H F 2-SOCF₂H F 3-SOCF₂H F 4-SOCF₂H F 2-SO₂CF₂H F 3-SO₂CF₂H F 4-SO₂CF₂H Br 2-CF₃ Br 3-CF₃ Br 4-CF₃ Br 2-OCF₃ Br 3-OCF₃ Br 4-OCF₃ Br 2-OCF₂H Br 3-OCF₂H Br 4-OCF₂H Br 2-OCF₂CF₂H Br 3-OCF₂CF₂H Br 4-OCF₂CF₂H Br 2-OCH₂CF₃ Br 3-OCH₂CF₃ Br 4-OCH₂CF₃ Br 2-SCF₃ Br 3-SCF₃ Br 4-SCF₃ Br 2-SOCF₃ Br 3-SOCF₃ Br 4-SOCF₃ Br 2-SO₂CF₃ Br 3-SO₂CF₃ Br 4-SO₂CF₃ Br 2-SCF₂H Br 3-SCF₂H Br 4-SCF₂H Br 2-SOCF₂H Br 3-SOCF₂H Br 4-SOCF₂H Br 2-SO₂CF₂H Br 3-SO₂CF₂H Br 4-SO₂CF₂H I 2-CF₃ I 3-CF₃ I 4-CF₃ I 2-OCF₃ I 3-OCF₃ I 4-OCF₃ I 2-OCF₂H I 3-OCF₂H I 4-OCF₂H I 2-OCF₂CF₂H I 3-OCF₂CF₂H I 4-OCF₂CF₂H I 2-OCH₂CF₃ I 3-OCH₂CF₃ I 4-OCH₂CF₃ I 2-SCF₃ I 3-SCF₃ I 4-SCF₃ I 2-SOCF₃ I 3-SOCF₃ I 4-SOCF₃ I 2-SO₂CF₃ I 3-SO₂CF₃ I 4-SO₂CF₃ I 2-SCF₂H I 3-SCF₂H I 4-SCF₂H I 2-SOCF₂H I 3-SOCF₂H I 4-SOCF₂H I 2-SO₂CF₂H I 3-SO₂CF₂H I 4-SO₂CF₂H OMe 2-CF₃ OMe 3-CF₃ OMe 4-CF₃ OMe 2-OCF₃ OMe 3-OCF₃ OMe 4-OCF₃ OMe 2-OCF₂H OMe 3-OCF₂H OMe 4-OCF₂H OMe 2-OCF₂CF₂H OMe 3-OCF₂CF₂H OMe 4-OCF₂CF₂H OMe 2-OCH₂CF₃ OMe 3-OCH₂CF₃ OMe 4-OCH₂CF₃ OMe 2-SCF₃ OMe 3-SCF₃ OMe 4-SCF₃ OMe 2-SOCF₃ OMe 3-SOCF₃ OMe 4-SOCF₃ OMe 2-SO₂CF₃ OMe 3-SO₂CF₃ OMe 4-SO₂CF₃ OMe 2-SCF₂H OMe 3-SCF₂H OMe 4-SCF₂H OMe 2-SOCF₂H OMe 3-SOCF₂H OMe 4-SOCF₂H OMe 2-SO₂CF₂H OMe 3-SO₂CF₂H OMe 4-SO₂CF₂H CF₃ 2-CF₃ CF₃ 3-CF₃ CF₃ 4-CF₃ CF₃ 2-OCF₃ CF₃ 3-OCF₃ CF₃ 4-OCF₃ CF₃ 2-OCF₂H CF₃ 3-OCF₂H CF₃ 4-OCF₂H CF₃ 2-OCF₂CF₂H CF₃ 3-OCF₂CF₂H CF₃ 4-OCF₂CF₂H CF₃ 2-OCH₂CF₃ CF₃ 3-OCH₂CF₃ CF₃ 4-OCH₂CF₃ CF₃ 2-SCF₃ CF₃ 3-SCF₃ CF₃ 4-SCF₃ CF₃ 2-SOCF₃ CF₃ 3-SOCF₃ CF₃ 4-SOCF₃ CF₃ 2-SO₂CF₃ CF₃ 3-SO₂CF₃ CF₃ 4-SO₂CF₃ CF₃ 2-SCF₂H CF₃ 3-SCF₂H CF₃ 4-SCF₂H CF₃ 2-SOCF₂H CF₃ 3-SOCF₂H CF₃ 4-SOCF₂H CF₃ 2-SO₂CF₂H CF₃ 3-SO₂CF₂H CF₃ 4-SO₂CF₂H OCF₂H 2-CF₃ OCF₂H 3-CF₃ OCF₂H 4-CF₃ OCF₂H 2-OCF₃ OCF₂H 3-OCF₃ OCF₂H 4-OCF₃ OCF₂H 2-OCF₂H OCF₂H 3-OCF₂H OCF₂H 4-OCF₂H OCF₂H 2-OCF₂CF₂H OCF₂H 3-OCF₂CF₂H OCF₂H 4-OCF₂CF₂H OCF₂H 2-OCH₂CF₃ OCF₂H 3-OCH₂CF₃ OCF₂H 4-OCH₂CF₃ OCF₂H 2-SCF₃ OCF₂H 3-SCF₃ OCF₂H 4-SCF₃ OCF₂H 2-SOCF₃ OCF₂H 3-SOCF₃ OCF₂H 4-SOCF₃ OCF₂H 2-SO₂CF₃ OCF₂H 3-SO₂CF₃ OCF₂H 4-SO₂CF₃ OCF₂H 2-SCF₂H OCF₂H 3-SCF₂H OCF₂H 4-SCF₂H OCF₂H 2-SOCF₂H OCF₂H 3-SOCF₂H OCF₂H 4-SOCF₂H OCF₂H 2-SO₂CF₂H OCF₂H 3-SO₂CF₂H OCF₂H 4-SO₂CF₂H Me 2-Me-4-CF₃ F 2-Me-4-CF₃ Cl 2-Me-4-CF₃ Me 2-Me-4-OCF₃ F 2-Me-4-OCF₃ Cl 2-Me-4-OCF₃ Me 2-Me-4-OCF₂H F 2-Me-4-OCF₂H Cl 2-Me-4-OCF₂H Me 2-Me-4-OCH₂CF₃ F 2-Me-4-OCH₂CF₃ Cl 2-Me-4-OCH₂CF₃ Me 2-Me-4-SCF₃ F 2-Me-4-SCF₃ Cl 2-Me-4-SCF₃ Me 2-Me-4-SOCF₃ F 2-Me-4-SOCF₃ Cl 2-Me-4-SOCF₃ Me 2-Me-4-SO₂CF₃ F 2-Me-4-SO₂CF₃ Cl 2-Me-4-SO₂CF₃ Me 2-Me-4-SCF₂H F 2-Me-4-SCF₂H Cl 2-Me-4-SCF₂H Me 2-Me-4-SOCF₂H F 2-Me-4-SOCF₂H Cl 2-Me-4-SOCF₂H Me 2-Me-4-SO₂CF₂H F 2-Me-4-SO₂CF₂H Cl 2-Me-4-SO₂CF₂H Br 2-Me-4-CF₃ I 2-Me-4-CF₃ OMe 2-Me-4-CF₃ Br 2-Me-4-OCF₃ I 2-Me-4-OCF₃ OMe 2-Me-4-OCF₃ Br 2-Me-4-OCF₂H I 2-Me-4-OCF₂H OMe 2-Me-4-OCF₂H Br 2-Me-4-OCH₂CF₃ I 2-Me-4-OCH₂CF₃ OMe 2-Me-4-OCH₂CF₃ Br 2-Me-4-SCF₃ I 2-Me-4-SCF₃ OMe 2-Me-4-SCF₃ Br 2-Me-4-SOCF₃ I 2-Me-4-SOCF₃ OMe 2-Me-4-SOCF₃ Br 2-Me-4-SO₂CF₃ I 2-Me-4-SO₂CF₃ OMe 2-Me-4-SO₂CF₃ Br 2-Me-4-SCF₂H I 2-Me-4-SCF₂H OMe 2-Me-4-SCF₂H Br 2-Me-4-SOCF₂H I 2-Me-4-SOCF₂H OMe 2-Me-4-SOCF₂H Br 2-Me-4-SO₂CF₂H I 2-Me-4-SO₂CF₂H OMe 2-Me-4-SO₂CF₂H CF₃ 2-Me-4-CF₃ NO₂ 2-Me-4-CF₃ SMe 2-Me-4-CF₃ CF₃ 2-Me-4-OCF₃ NO₂ 2-Me-4-OCF₃ SMe 2-Me-4-OCF₃ CF₃ 2-Me-4-OCF₂H NO₂ 2-Me-4-OCF₂H SMe 2-Me-4-OCF₂H CF₃ 2-Me-4-OCH₂CF₃ NO₂ 2-Me-4-OCH₂CF₃ SMe 2-Me-4-OCH₂CF₃ CF₃ 2-Me-4-SCF₃ NO₂ 2-Me-4-SCF₃ SMe 2-Me-4-SCF₃ CF₃ 2-Me-4-SOCF₃ NO₂ 2-Me-4-SOCF₃ SMe 2-Me-4-SOCF₃ CF₃ 2-Me-4-SO₂CF₃ NO₂ 2-Me-4-SO₂CF₃ SMe 2-Me-4-SO₂CF₃ CF₃ 2-Me-4-SCF₂H NO₂ 2-Me-4-SCF₂H SMe 2-Me-4-SCF₂H CF₃ 2-Me-4-SOCF₂H NO₂ 2-Me-4-SOCF₂H SMe 2-Me-4-SOCF₂H CF₃ 2-Me-4-SO₂CF₂H NO₂ 2-Me-4-SO₂CF₂H SMe 2-Me-4-SO₂CF₂H

TABLE 2

R⁴ R⁵ and/or R⁶ R⁴ R⁵ and/or R⁶ R⁴ R⁵ and/or R⁶ Me 2-CF₃ Me 3-CF₃ Me 4-CF₃ Me 2-OCF₃ Me 3-OCF₃ Me 4-OCF₃ Me 2-OCF₂H Me 3-OCF₂H Me 4-OCF₂H Me 2-OCF₂CF₂H Me 3-OCF₂CF₂H Me 4-OCF₂CF₂H Me 2-OCH₂CF₃ Me 3-OCH₂CF₃ Me 4-OCH₂CF₃ Me 2-SCF₃ Me 3-SCF₃ Me 4-SCF₃ Me 2-SOCF₃ Me 3-SOCF₃ Me 4-SOCF₃ Me 2-SO₂CF₃ Me 3-SO₂CF₃ Me 4-SO₂CF₃ Me 2-SCF₂H Me 3-SCF₂H Me 4-SCF₂H Me 2-SOCF₂H Me 3-SOCF₂H Me 4-SOCF₂H Me 2-SO₂CF₂H Me 3-SO₂CF₂H Me 4-SO₂CF₂H Cl 2-CF₃ Cl 3-CF₃ Cl 4-CF₃ Cl 2-OCF₃ Cl 3-OCF₃ Cl 4-OCF₃ Cl 2-OCF₂H Cl 3-OCF₂H Cl 4-OCF₂H Cl 2-OCF₂CF₂H Cl 3-OCF₂CF₂H Cl 4-OCF₂CF₂H Cl 2-OCH₂CF₃ Cl 3-OCH₂CF₃ Cl 4-OCH₂CF₃ Cl 2-SCF₃ Cl 3-SCF₃ Cl 4-SCF₃ Cl 2-SOCF₃ Cl 3-SOCF₃ Cl 4-SOCF₃ Cl 2-SO₂CF₃ Cl 3-SO₂CF₃ Cl 4-SO₂CF₃ Cl 2-SCF₂H Cl 3-SCF₂H Cl 4-SCF₂H Cl 2-SOCF₂H Cl 3-SOCF₂H Cl 4-SOCF₂H Cl 2-SO₂CF₂H Cl 3-SO₂CF₂H Cl 4-SO₂CF₂H F 2-CF₃ F 3-CF₃ F 4-CF₃ F 2-OCF₃ F 3-OCF₃ F 4-OCF₃ F 2-OCF₂H F 3-OCF₂H F 4-OCF₂H F 2-OCF₂CF₂H F 3-OCF₂CF₂H F 4-OCF₂CF₂H F 2-OCH₂CF₃ F 3-OCH₂CF₃ F 4-OCH₂CF₃ F 2-SCF₃ F 3-SCF₃ F 4-SCF₃ F 2-SOCF₃ F 3-SOCF₃ F 4-SOCF₃ F 2-SO₂CF₃ F 3-SO₂CF₃ F 4-SO₂CF₃ F 2-SCF₂H F 3-SCF₂H F 4-SCF₂H F 2-SOCF₂H F 3-SOCF₂H F 4-SOCF₂H F 2-SO₂CF₂H F 3-SO₂CF₂H F 4-SO₂CF₂H Br 2-CF₃ Br 3-CF₃ Br 4-CF₃ Br 2-OCF₃ Br 3-OCF₃ Br 4-OCF₃ Br 2-OCF₂H Br 3-OCF₂H Br 4-OCF₂H Br 2-OCF₂CF₂H Br 3-OCF₂CF₂H Br 4-OCF₂CF₂H Br 2-OCH₂CF₃ Br 3-OCH₂CF₃ Br 4-OCH₂CF₃ Br 2-SCF₃ Br 3-SCF₃ Br 4-SCF₃ Br 2-SOCF₃ Br 3-SOCF₃ Br 4-SOCF₃ Br 2-SO₂CF₃ Br 3-SO₂CF₃ Br 4-SO₂CF₃ Br 2-SCF₂H Br 3-SCF₂H Br 4-SCF₂H Br 2-SOCF₂H Br 3-SOCF₂H Br 4-SOCF₂H Br 2-SO₂CF₂H Br 3-SO₂CF₂H Br 4-SO₂CF₂H I 2-CF₃ I 3-CF₃ I 4-CF₃ I 2-OCF₃ I 3-OCF₃ I 4-OCF₃ I 2-OCF₂H I 3-OCF₂H I 4-OCF₂H I 2-OCF₂CF₂H I 3-OCF₂CF₂H I 4-OCF₂CF₂H I 2-OCH₂CF₃ I 3-OCH₂CF₃ I 4-OCH₂CF₃ I 2-SCF₃ I 3-SCF₃ I 4-SCF₃ I 2-SOCF₃ I 3-SOCF₃ I 4-SOCF₃ I 2-SO₂CF₃ I 3-SO₂CF₃ I 4-SO₂CF₃ I 2-SCF₂H I 3-SCF₂H I 4-SCF₂H I 2-SOCF₂H I 3-SOCF₂H I 4-SOCF₂H I 2-SO₂CF₂H I 3-SO₂CF₂H I 4-SO₂CF₂H OMe 2-CF₃ OMe 3-CF₃ OMe 4-CF₃ OMe 2-OCF₃ OMe 3-OCF₃ OMe 4-OCF₃ OMe 2-OCF₂H OMe 3-OCF₂H OMe 4-OCF₂H OMe 2-OCF₂CF₂H OMe 3-OCF₂CF₂H OMe 4-OCF₂CF₂H OMe 2-OCH₂CF₃ OMe 3-OCH₂CF₃ OMe 4-OCH₂CF₃ OMe 2-SCF₃ OMe 3-SCF₃ OMe 4-SCF₃ OMe 2-SOCF₃ OMe 3-SOCF₃ OMe 4-SOCF₃ OMe 2-SO₂CF₃ OMe 3-SO₂CF₃ OMe 4-SO₂CF₃ OMe 2-SCF₂H OMe 3-SCF₂H OMe 4-SCF₂H OMe 2-SOCF₂H OMe 3-SOCF₂H OMe 4-SOCF₂H OMe 2-SO₂CF₂H OMe 3-SO₂CF₂H OMe 4-SO₂CF₂H CF₃ 2-CF₃ CF₃ 3-CF₃ CF₃ 4-CF₃ CF₃ 2-OCF₃ CF₃ 3-OCF₃ CF₃ 4-OCF₃ CF₃ 2-OCF₂H CF₃ 3-OCF₂H CF₃ 4-OCF₂H CF₃ 2-OCF₂CF₂H CF₃ 3-OCF₂CF₂H CF₃ 4-OCF₂CF₂H CF₃ 2-OCH₂CF₃ CF₃ 3-OCH₂CF₃ CF₃ 4-OCH₂CF₃ CF₃ 2-SCF₃ CF₃ 3-SCF₃ CF₃ 4-SCF₃ CF₃ 2-SOCF₃ CF₃ 3-SOCF₃ CF₃ 4-SOCF₃ CF₃ 2-SO₂CF₃ CF₃ 3-SO₂CF₃ CF₃ 4-SO₂CF₃ CF₃ 2-SCF₂H CF₃ 3-SCF₂H CF₃ 4-SCF₂H CF₃ 2-SOCF₂H CF₃ 3-SOCF₂H CF₃ 4-SOCF₂H CF₃ 2-SO₂CF₂H CF₃ 3-SO₂CF₂H CF₃ 4-SO₂CF₂H OCF₂H 2-CF₃ OCF₂H 3-CF₃ OCF₂H 4-CF₃ OCF₂H 2-OCF₃ OCF₂H 3-OCF₃ OCF₂H 4-OCF₃ OCF₂H 2-OCF₂H OCF₂H 3-OCF₂H OCF₂H 4-OCF₂H OCF₂H 2-OCF₂CF₂H OCF₂H 3-OCF₂CF₂H OCF₂H 4-OCF₂CF₂H OCF₂H 2-OCH₂CF₃ OCF₂H 3-OCH₂CF₃ OCF₂H 4-OCH₂CF₃ OCF₂H 2-SCF₃ OCF₂H 3-SCF₃ OCF₂H 4-SCF₃ OCF₂H 2-SOCF₃ OCF₂H 3-SOCF₃ OCF₂H 4-SOCF₃ OCF₂H 2-SO₂CF₃ OCF₂H 3-SO₂CF₃ OCF₂H 4-SO₂CF₃ OCF₂H 2-SCF₂H OCF₂H 3-SCF₂H OCF₂H 4-SCF₂H OCF₂H 2-SOCF₂H OCF₂H 3-SOCF₂H OCF₂H 4-SOCF₂H OCF₂H 2-SO₂CF₂H OCF₂H 3-SO₂CF₂H OCF₂H 4-SO₂CF₂H Me 2-Me-4-CF₃ F 2-Me-4-CF₃ Cl 2-Me-4-CF₃ Me 2-Me-4-OCF₃ F 2-Me-4-OCF₃ Cl 2-Me-4-OCF₃ Me 2-Me-4-OCF₂H F 2-Me-4-OCF₂H Cl 2-Me-4-OCF₂H Me 2-Me-4-OCH₂CF₃ F 2-Me-4-OCH₂CF₃ Cl 2-Me-4-OCH₂CF₃ Me 2-Me-4-SCF₃ F 2-Me-4-SCF₃ Cl 2-Me-4-SCF₃ Me 2-Me-4-SOCF₃ F 2-Me-4-SOCF₃ Cl 2-Me-4-SOCF₃ Me 2-Me-4-SO₂CF₃ F 2-Me-4-SO₂CF₃ Cl 2-Me-4-SO₂CF₃ Me 2-Me-4-SCF₂H F 2-Me-4-SCF₂H Cl 2-Me-4-SCF₂H Me 2-Me-4-SOCF₂H F 2-Me-4-SOCF₂H Cl 2-Me-4-SOCF₂H Me 2-Me-4-SO₂CF₂H F 2-Me-4-SO₂CF₂H Cl 2-Me-4-SO₂CF₂H Br 2-Me-4-CF₃ I 2-Me-4-CF₃ OMe 2-Me-4-CF₃ Br 2-Me-4-OCF₃ I 2-Me-4-OCF₃ OMe 2-Me-4-OCF₃ Br 2-Me-4-OCF₂H I 2-Me-4-OCF₂H OMe 2-Me-4-OCF₂H Br 2-Me-4-OCH₂CF₃ I 2-Me-4-OCH₂CF₃ OMe 2-Me-4-OCH₂CF₃ Br 2-Me-4-SCF₃ I 2-Me-4-SCF₃ OMe 2-Me-4-SCF₃ Br 2-Me-4-SOCF₃ I 2-Me-4-SOCF₃ OMe 2-Me-4-SOCF₃ Br 2-Me-4-SO₂CF₃ I 2-Me-4-SO₂CF₃ OMe 2-Me-4-SO₂CF₃ Br 2-Me-4-SCF₂H I 2-Me-4-SCF₂H OMe 2-Me-4-SCF₂H Br 2-Me-4-SOCF₂H I 2-Me-4-SOCF₂H OMe 2-Me-4-SOCF₂H Br 2-Me-4-SO₂CF₂H I 2-Me-4-SO₂CF₂H OMe 2-Me-4-SO₂CF₂H CF₃ 2-Me-4-CF₃ NO₂ 2-Me-4-CF₃ SMe 2-Me-4-CF₃ CF₃ 2-Me-4-OCF₃ NO₂ 2-Me-4-OCF₃ SMe 2-Me-4-OCF₃ CF₃ 2-Me-4-OCF₂H NO₂ 2-Me-4-OCF₂H SMe 2-Me-4-OCF₂H CF₃ 2-Me-4-OCH₂CF₃ NO₂ 2-Me-4-OCH₂CF₃ SMe 2-Me-4-OCH₂CF₃ CF₃ 2-Me-4-SCF₃ NO₂ 2-Me-4-SCF₃ SMe 2-Me-4-SCF₃ CF₃ 2-Me-4-SOCF₃ NO₂ 2-Me-4-SOCF₃ SMe 2-Me-4-SOCF₃ CF₃ 2-Me-4-SO₂CF₃ NO₂ 2-Me-4-SO₂CF₃ SMe 2-Me-4-SO₂CF₃ CF₃ 2-Me-4-SCF₂H NO₂ 2-Me-4-SCF₂H SMe 2-Me-4-SCF₂H CF₃ 2-Me-4-SOCF₂H NO₂ 2-Me-4-SOCF₂H SMe 2-Me-4-SOCF₂H CF₃ 2-Me-4-SO₂CF₂H NO₂ 2-Me-4-SO₂CF₂H SMe 2-Me-4-SO₂CF₂H

TABLE 3

R⁴ R⁵ and/or R⁶ R⁴ R⁵ and/or R⁶ R⁴ R⁵ and/or R⁶ Me 2-CF₃ Me 3-CF₃ Me 4-CF₃ Me 2-OCF₃ Me 3-OCF₃ Me 4-OCF₃ Me 2-OCF₂H Me 3-OCF₂H Me 4-OCF₂H Me 2-OCF₂CF₂H Me 3-OCF₂CF₂H Me 4-OCF₂CF₂H Me 2-OCH₂CF₃ Me 3-OCH₂CF₃ Me 4-OCH₂CF₃ Me 2-SCF₃ Me 3-SCF₃ Me 4-SCF₃ Me 2-SOCF₃ Me 3-SOCF₃ Me 4-SOCF₃ Me 2-SO₂CF₃ Me 3-SO₂CF₃ Me 4-SO₂CF₃ Me 2-SCF₂H Me 3-SCF₂H Me 4-SCF₂H Me 2-SOCF₂H Me 3-SOCF₂H Me 4-SOCF₂H Me 2-SO₂CF₂H Me 3-SO₂CF₂H Me 4-SO₂CF₂H Cl 2-CF₃ Cl 3-CF₃ Cl 4-CF₃ Cl 2-OCF₃ Cl 3-OCF₃ Cl 4-OCF₃ Cl 2-OCF₂H Cl 3-OCF₂H Cl 4-OCF₂H Cl 2-OCF₂CF₂H Cl 3-OCF₂CF₂H Cl 4-OCF₂CF₂H Cl 2-OCH₂CF₃ Cl 3-OCH₂CF₃ Cl 4-OCH₂CF₃ Cl 2-SCF₃ Cl 3-SCF₃ Cl 4-SCF₃ Cl 2-SOCF₃ Cl 3-SOCF₃ Cl 4-SOCF₃ Cl 2-SO₂CF₃ Cl 3-SO₂CF₃ Cl 4-SO₂CF₃ Cl 2-SCF₂H Cl 3-SCF₂H Cl 4-SCF₂H Cl 2-SOCF₂H Cl 3-SOCF₂H Cl 4-SOCF₂H Cl 2-SO₂CF₂H Cl 3-SO₂CF₂H Cl 4-SO₂CF₂H F 2-CF₃ F 3-CF₃ F 4-CF₃ F 2-OCF₃ F 3-OCF₃ F 4-OCF₃ F 2-OCF₂H F 3-OCF₂H F 4-OCF₂H F 2-OCF₂CF₂H F 3-OCF₂CF₂H F 4-OCF₂CF₂H F 2-OCH₂CF₃ F 3-OCH₂CF₃ F 4-OCH₂CF₃ F 2-SCF₃ F 3-SCF₃ F 4-SCF₃ F 2-SOCF₃ F 3-SOCF₃ F 4-SOCF₃ F 2-SO₂CF₃ F 3-SO₂CF₃ F 4-SO₂CF₃ F 2-SCF₂H F 3-SCF₂H F 4-SCF₂H F 2-SOCF₂H F 3-SOCF₂H F 4-SOCF₂H F 2-SO₂CF₂H F 3-SO₂CF₂H F 4-SO₂CF₂H Br 2-CF₃ Br 3-CF₃ Br 4-CF₃ Br 2-OCF₃ Br 3-OCF₃ Br 4-OCF₃ Br 2-OCF₂H Br 3-OCF₂H Br 4-OCF₂H Br 2-OCF₂CF₂H Br 3-OCF₂CF₂H Br 4-OCF₂CF₂H Br 2-OCH₂CF₃ Br 3-OCH₂CF₃ Br 4-OCH₂CF₃ Br 2-SCF₃ Br 3-SCF₃ Br 4-SCF₃ Br 2-SOCF₃ Br 3-SOCF₃ Br 4-SOCF₃ Br 2-SO₂CF₃ Br 3-SO₂CF₃ Br 4-SO₂CF₃ Br 2-SCF₂H Br 3-SCF₂H Br 4-SCF₂H Br 2-SOCF₂H Br 3-SOCF₂H Br 4-SOCF₂H Br 2-SO₂CF₂H Br 3-SO₂CF₂H Br 4-SO₂CF₂H I 2-CF₃ I 3-CF₃ I 4-CF₃ I 2-OCF₃ I 3-OCF₃ I 4-OCF₃ I 2-OCF₂H I 3-OCF₂H I 4-OCF₂H I 2-OCF₂CF₂H I 3-OCF₂CF₂H I 4-OCF₂CF₂H I 2-OCH₂CF₃ I 3-OCH₂CF₃ I 4-OCH₂CF₃ I 2-SCF₃ I 3-SCF₃ I 4-SCF₃ I 2-SOCF₃ I 3-SOCF₃ I 4-SOCF₃ I 2-SO₂CF₃ I 3-SO₂CF₃ I 4-SO₂CF₃ I 2-SCF₂H I 3-SCF₂H I 4-SCF₂H I 2-SOCF₂H I 3-SOCF₂H I 4-SOCF₂H I 2-SO₂CF₂H I 3-SO₂CF₂H I 4-SO₂CF₂H OMe 2-CF₃ OMe 3-CF₃ OMe 4-CF₃ OMe 2-OCF₃ OMe 3-OCF₃ OMe 4-OCF₃ OMe 2-OCF₂H OMe 3-OCF₂H OMe 4-OCF₂H OMe 2-OCF₂CF₂H OMe 3-OCF₂CF₂H OMe 4-OCF₂CF₂H OMe 2-OCH₂CF₃ OMe 3-OCH₂CF₃ OMe 4-OCH₂CF₃ OMe 2-SCF₃ OMe 3-SCF₃ OMe 4-SCF₃ OMe 2-SOCF₃ OMe 3-SOCF₃ OMe 4-SOCF₃ OMe 2-SO₂CF₃ OMe 3-SO₂CF₃ OMe 4-SO₂CF₃ OMe 2-SCF₂H OMe 3-SCF₂H OMe 4-SCF₂H OMe 2-SOCF₂H OMe 3-SOCF₂H OMe 4-SOCF₂H OMe 2-SO₂CF₂H OMe 3-SO₂CF₂H OMe 4-SO₂CF₂H CF₃ 2-CF₃ CF₃ 3-CF₃ CF₃ 4-CF₃ CF₃ 2-OCF₃ CF₃ 3-OCF₃ CF₃ 4-OCF₃ CF₃ 2-OCF₂H CF₃ 3-OCF₂H CF₃ 4-OCF₂H CF₃ 2-OCF₂CF₂H CF₃ 3-OCF₂CF₂H CF₃ 4-OCF₂CF₂H CF₃ 2-OCH₂CF₃ CF₃ 3-OCH₂CF₃ CF₃ 4-OCH₂CF₃ CF₃ 2-SCF₃ CF₃ 3-SCF₃ CF₃ 4-SCF₃ CF₃ 2-SOCF₃ CF₃ 3-SOCF₃ CF₃ 4-SOCF₃ CF₃ 2-SO₂CF₃ CF₃ 3-SO₂CF₃ CF₃ 4-SO₂CF₃ CF₃ 2-SCF₂H CF₃ 3-SCF₂H CF₃ 4-SCF₂H CF₃ 2-SOCF₂H CF₃ 3-SOCF₂H CF₃ 4-SOCF₂H CF₃ 2-SO₂CF₂H CF₃ 3-SO₂CF₂H CF₃ 4-SO₂CF₂H OCF₂H 2-CF₃ OCF₂H 3-CF₃ OCF₂H 4-CF₃ OCF₂H 2-OCF₃ OCF₂H 3-OCF₃ OCF₂H 4-OCF₃ OCF₂H 2-OCF₂H OCF₂H 3-OCF₂H OCF₂H 4-OCF₂H OCF₂H 2-OCF₂CF₂H OCF₂H 3-OCF₂CF₂H OCF₂H 4-OCF₂CF₂H OCF₂H 2-OCH₂CF₃ OCF₂H 3-OCH₂CF₃ OCF₂H 4-OCH₂CF₃ OCF₂H 2-SCF₃ OCF₂H 3-SCF₃ OCF₂H 4-SCF₃ OCF₂H 2-SOCF₃ OCF₂H 3-SOCF₃ OCF₂H 4-SOCF₃ OCF₂H 2-SO₂CF₃ OCF₂H 3-SO₂CF₃ OCF₂H 4-SO₂CF₃ OCF₂H 2-SCF₂H OCF₂H 3-SCF₂H OCF₂H 4-SCF₂H OCF₂H 2-SOCF₂H OCF₂H 3-SOCF₂H OCF₂H 4-SOCF₂H OCF₂H 2-SO₂CF₂H OCF₂H 3-SO₂CF₂H OCF₂H 4-SO₂CF₂H Me 2-Me-4-CF₃ F 2-Me-4-CF₃ Cl 2-Me-4-CF₃ Me 2-Me-4-OCF₃ F 2-Me-4-OCF₃ Cl 2-Me-4-OCF₃ Me 2-Me-4-OCF₂H F 2-Me-4-OCF₂H Cl 2-Me-4-OCF₂H Me 2-Me-4-OCH₂CF₃ F 2-Me-4-OCH₂CF₃ Cl 2-Me-4-OCH₂CF₃ Me 2-Me-4-SCF₃ F 2-Me-4-SCF₃ Cl 2-Me-4-SCF₃ Me 2-Me-4-SOCF₃ F 2-Me-4-SOCF₃ Cl 2-Me-4-SOCF₃ Me 2-Me-4-SO₂CF₃ F 2-Me-4-SO₂CF₃ Cl 2-Me-4-SO₂CF₃ Me 2-Me-4-SCF₂H F 2-Me-4-SCF₂H Cl 2-Me-4-SCF₂H Me 2-Me-4-SOCF₂H F 2-Me-4-SOCF₂H Cl 2-Me-4-SOCF₂H Me 2-Me-4-SO₂CF₂H F 2-Me-4-SO₂CF₂H Cl 2-Me-4-SO₂CF₂H Br 2-Me-4-CF₃ I 2-Me-4-CF₃ OMe 2-Me-4-CF₃ Br 2-Me-4-OCF₃ I 2-Me-4-OCF₃ OMe 2-Me-4-OCF₃ Br 2-Me-4-OCF₂H I 2-Me-4-OCF₂H OMe 2-Me-4-OCF₂H Br 2-Me-4-OCH₂CF₃ I 2-Me-4-OCH₂CF₃ OMe 2-Me-4-OCH₂CF₃ Br 2-Me-4-SCF₃ I 2-Me-4-SCF₃ OMe 2-Me-4-SCF₃ Br 2-Me-4-SOCF₃ I 2-Me-4-SOCF₃ OMe 2-Me-4-SOCF₃ Br 2-Me-4-SO₂CF₃ I 2-Me-4-SO₂CF₃ OMe 2-Me-4-SO₂CF₃ Br 2-Me-4-SCF₂H I 2-Me-4-SCF₂H OMe 2-Me-4-SCF₂H Br 2-Me-4-SOCF₂H I 2-Me-4-SOCF₂H OMe 2-Me-4-SOCF₂H Br 2-Me-4-SO₂CF₂H I 2-Me-4-SO₂CF₂H OMe 2-Me-4-SO₂CF₂H CF₃ 2-Me-4-CF₃ NO₂ 2-Me-4-CF₃ SMe 2-Me-4-CF₃ CF₃ 2-Me-4-OCF₃ NO₂ 2-Me-4-OCF₃ SMe 2-Me-4-OCF₃ CF₃ 2-Me-4-OCF₂H NO₂ 2-Me-4-OCF₂H SMe 2-Me-4-OCF₂H CF₃ 2-Me-4-OCH₂CF₃ NO₂ 2-Me-4-OCH₂CF₃ SMe 2-Me-4-OCH₂CF₃ CF₃ 2-Me-4-SCF₃ NO₂ 2-Me-4-SCF₃ SMe 2-Me-4-SCF₃ CF₃ 2-Me-4-SOCF₃ NO₂ 2-Me-4-SOCF₃ SMe 2-Me-4-SOCF₃ CF₃ 2-Me-4-SO₂CF₃ NO₂ 2-Me-4-SO₂CF₃ SMe 2-Me-4-SO₂CF₃ CF₃ 2-Me-4-SCF₂H NO₂ 2-Me-4-SCF₂H SMe 2-Me-4-SCF₂H CF₃ 2-Me-4-SOCF₂H NO₂ 2-Me-4-SOCF₂H SMe 2-Me-4-SOCF₂H CF₃ 2-Me-4-SO₂CF₂H NO₂ 2-Me-4-SO₂CF₂H SMe 2-Me-4-SO₂CF₂H

TABLE 4

R⁴ R⁵ and/or R⁶ R⁴ R⁵ and/or R⁶ R⁴ R⁵ and/or R⁶ Me 2-CF₃ Me 3-CF₃ Me 4-CF₃ Me 2-OCF₃ Me 3-OCF₃ Me 4-OCF₃ Me 2-OCF₂H Me 3-OCF₂H Me 4-OCF₂H Me 2-OCF₂CF₂H Me 3-OCF₂CF₂H Me 4-OCF₂CF₂H Me 2-OCH₂CF₃ Me 3-OCH₂CF₃ Me 4-OCH₂CF₃ Me 2-SCF₃ Me 3-SCF₃ Me 4-SCF₃ Me 2-SOCF₃ Me 3-SOCF₃ Me 4-SOCF₃ Me 2-SO₂CF₃ Me 3-SO₂CF₃ Me 4-SO₂CF₃ Me 2-SCF₂H Me 3-SCF₂H Me 4-SCF₂H Me 2-SOCF₂H Me 3-SOCF₂H Me 4-SOCF₂H Me 2-SO₂CF₂H Me 3-SO₂CF₂H Me 4-SO₂CF₂H Cl 2-CF₃ Cl 3-CF₃ Cl 4-CF₃ Cl 2-OCF₃ Cl 3-OCF₃ Cl 4-OCF₃ Cl 2-OCF₂H Cl 3-OCF₂H Cl 4-OCF₂H Cl 2-OCF₂CF₂H Cl 3-OCF₂CF₂H Cl 4-OCF₂CF₂H Cl 2-OCH₂CF₃ Cl 3-OCH₂CF₃ Cl 4-OCH₂CF₃ Cl 2-SCF₃ Cl 3-SCF₃ Cl 4-SCF₃ Cl 2-SOCF₃ Cl 3-SOCF₃ Cl 4-SOCF₃ Cl 2-SO₂CF₃ Cl 3-SO₂CF₃ Cl 4-SO₂CF₃ Cl 2-SCF₂H Cl 3-SCF₂H Cl 4-SCF₂H Cl 2-SOCF₂H Cl 3-SOCF₂H Cl 4-SOCF₂H Cl 2-SO₂CF₂H Cl 3-SO₂CF₂H Cl 4-SO₂CF₂H F 2-CF₃ F 3-CF₃ F 4-CF₃ F 2-OCF₃ F 3-OCF₃ F 4-OCF₃ F 2-OCF₂H F 3-OCF₂H F 4-OCF₂H F 2-OCF₂CF₂H F 3-OCF₂CF₂H F 4-OCF₂CF₂H F 2-OCH₂CF₃ F 3-OCH₂CF₃ F 4-OCH₂CF₃ F 2-SCF₃ F 3-SCF₃ F 4-SCF₃ F 2-SOCF₃ F 3-SOCF₃ F 4-SOCF₃ F 2-SO₂CF₃ F 3-SO₂CF₃ F 4-SO₂CF₃ F 2-SCF₂H F 3-SCF₂H F 4-SCF₂H F 2-SOCF₂H F 3-SOCF₂H F 4-SOCF₂H F 2-SO₂CF₂H F 3-SO₂CF₂H F 4-SO₂CF₂H Br 2-CF₃ Br 3-CF₃ Br 4-CF₃ Br 2-OCF₃ Br 3-OCF₃ Br 4-OCF₃ Br 2-OCF₂H Br 3-OCF₂H Br 4-OCF₂H Br 2-OCF₂CF₂H Br 3-OCF₂CF₂H Br 4-OCF₂CF₂H Br 2-OCH₂CF₃ Br 3-OCH₂CF₃ Br 4-OCH₂CF₃ Br 2-SCF₃ Br 3-SCF₃ Br 4-SCF₃ Br 2-SOCF₃ Br 3-SOCF₃ Br 4-SOCF₃ Br 2-SO₂CF₃ Br 3-SO₂CF₃ Br 4-SO₂CF₃ Br 2-SCF₂H Br 3-SCF₂H Br 4-SCF₂H Br 2-SOCF₂H Br 3-SOCF₂H Br 4-SOCF₂H Br 2-SO₂CF₂H Br 3-SO₂CF₂H Br 4-SO₂CF₂H I 2-CF₃ I 3-CF₃ I 4-CF₃ I 2-OCF₃ I 3-OCF₃ I 4-OCF₃ I 2-OCF₂H I 3-OCF₂H I 4-OCF₂H I 2-OCF₂CF₂H I 3-OCF₂CF₂H I 4-OCF₂CF₂H I 2-OCH₂CF₃ I 3-OCH₂CF₃ I 4-OCH₂CF₃ I 2-SCF₃ I 3-SCF₃ I 4-SCF₃ I 2-SOCF₃ I 3-SOCF₃ I 4-SOCF₃ I 2-SO₂CF₃ I 3-SO₂CF₃ I 4-SO₂CF₃ I 2-SCF₂H I 3-SCF₂H I 4-SCF₂H I 2-SOCF₂H I 3-SOCF₂H I 4-SOCF₂H I 2-SO₂CF₂H I 3-SO₂CF₂H I 4-SO₂CF₂H OMe 2-CF₃ OMe 3-CF₃ OMe 4-CF₃ OMe 2-OCF₃ OMe 3-OCF₃ OMe 4-OCF₃ OMe 2-OCF₂H OMe 3-OCF₂H OMe 4-OCF₂H OMe 2-OCF₂CF₂H OMe 3-OCF₂CF₂H OMe 4-OCF₂CF₂H OMe 2-OCH₂CF₃ OMe 3-OCH₂CF₃ OMe 4-OCH₂CF₃ OMe 2-SCF₃ OMe 3-SCF₃ OMe 4-SCF₃ OMe 2-SOCF₃ OMe 3-SOCF₃ OMe 4-SOCF₃ OMe 2-SO₂CF₃ OMe 3-SO₂CF₃ OMe 4-SO₂CF₃ OMe 2-SCF₂H OMe 3-SCF₂H OMe 4-SCF₂H OMe 2-SOCF₂H OMe 3-SOCF₂H OMe 4-SOCF₂H OMe 2-SO₂CF₂H OMe 3-SO₂CF₂H OMe 4-SO₂CF₂H CF₃ 2-CF₃ CF₃ 3-CF₃ CF₃ 4-CF₃ CF₃ 2-OCF₃ CF₃ 3-OCF₃ CF₃ 4-OCF₃ CF₃ 2-OCF₂H CF₃ 3-OCF₂H CF₃ 4-OCF₂H CF₃ 2-OCF₂CF₂H CF₃ 3-OCF₂CF₂H CF₃ 4-OCF₂CF₂H CF₃ 2-OCH₂CF₃ CF₃ 3-OCH₂CF₃ CF₃ 4-OCH₂CF₃ CF₃ 2-SCF₃ CF₃ 3-SCF₃ CF₃ 4-SCF₃ CF₃ 2-SOCF₃ CF₃ 3-SOCF₃ CF₃ 4-SOCF₃ CF₃ 2-SO₂CF₃ CF₃ 3-SO₂CF₃ CF₃ 4-SO₂CF₃ CF₃ 2-SCF₂H CF₃ 3-SCF₂H CF₃ 4-SCF₂H CF₃ 2-SOCF₂H CF₃ 3-SOCF₂H CF₃ 4-SOCF₂H CF₃ 2-SO₂CF₂H CF₃ 3-SO₂CF₂H CF₃ 4-SO₂CF₂H OCF₂H 2-CF₃ OCF₂H 3-CF₃ OCF₂H 4-CF₃ OCF₂H 2-OCF₃ OCF₂H 3-OCF₃ OCF₂H 4-OCF₃ OCF₂H 2-OCF₂H OCF₂H 3-OCF₂H OCF₂H 4-OCF₂H OCF₂H 2-OCF₂CF₂H OCF₂H 3-OCF₂CF₂H OCF₂H 4-OCF₂CF₂H OCF₂H 2-OCH₂CF₃ OCF₂H 3-OCH₂CF₃ OCF₂H 4-OCH₂CF₃ OCF₂H 2-SCF₃ OCF₂H 3-SCF₃ OCF₂H 4-SCF₃ OCF₂H 2-SOCF₃ OCF₂H 3-SOCF₃ OCF₂H 4-SOCF₃ OCF₂H 2-SO₂CF₃ OCF₂H 3-SO₂CF₃ OCF₂H 4-SO₂CF₃ OCF₂H 2-SCF₂H OCF₂H 3-SCF₂H OCF₂H 4-SCF₂H OCF₂H 2-SOCF₂H OCF₂H 3-SOCF₂H OCF₂H 4-SOCF₂H OCF₂H 2-SO₂CF₂H OCF₂H 3-SO₂CF₂H OCF₂H 4-SO₂CF₂H Me 2-Me-4-CF₃ F 2-Me-4-CF₃ Cl 2-Me-4-CF₃ Me 2-Me-4-OCF₃ F 2-Me-4-OCF₃ Cl 2-Me-4-OCF₃ Me 2-Me-4-OCF₂H F 2-Me-4-OCF₂H Cl 2-Me-4-OCF₂H Me 2-Me-4-OCH₂CF₃ F 2-Me-4-OCH₂CF₃ Cl 2-Me-4-OCH₂CF₃ Me 2-Me-4-SCF₃ F 2-Me-4-SCF₃ Cl 2-Me-4-SCF₃ Me 2-Me-4-SOCF₃ F 2-Me-4-SOCF₃ Cl 2-Me-4-SOCF₃ Me 2-Me-4-SO₂CF₃ F 2-Me-4-SO₂CF₃ Cl 2-Me-4-SO₂CF₃ Me 2-Me-4-SCF₂H F 2-Me-4-SCF₂H Cl 2-Me-4-SCF₂H Me 2-Me-4-SOCF₂H F 2-Me-4-SOCF₂H Cl 2-Me-4-SOCF₂H Me 2-Me-4-SO₂CF₂H F 2-Me-4-SO₂CF₂H Cl 2-Me-4-SO₂CF₂H Br 2-Me-4-CF₃ I 2-Me-4-CF₃ OMe 2-Me-4-CF₃ Br 2-Me-4-OCF₃ I 2-Me-4-OCF₃ OMe 2-Me-4-OCF₃ Br 2-Me-4-OCF₂H I 2-Me-4-OCF₂H OMe 2-Me-4-OCF₂H Br 2-Me-4-OCH₂CF₃ I 2-Me-4-OCH₂CF₃ OMe 2-Me-4-OCH₂CF₃ Br 2-Me-4-SCF₃ I 2-Me-4-SCF₃ OMe 2-Me-4-SCF₃ Br 2-Me-4-SOCF₃ I 2-Me-4-SOCF₃ OMe 2-Me-4-SOCF₃ Br 2-Me-4-SO₂CF₃ I 2-Me-4-SO₂CF₃ OMe 2-Me-4-SO₂CF₃ Br 2-Me-4-SCF₂H I 2-Me-4-SCF₂H OMe 2-Me-4-SCF₂H Br 2-Me-4-SOCF₂H I 2-Me-4-SOCF₂H OMe 2-Me-4-SOCF₂H Br 2-Me-4-SO₂CF₂H I 2-Me-4-SO₂CF₂H OMe 2-Me-4-SO₂CF₂H CF₃ 2-Me-4-CF₃ NO₂ 2-Me-4-CF₃ SMe 2-Me-4-CF₃ CF₃ 2-Me-4-OCF₃ NO₂ 2-Me-4-OCF₃ SMe 2-Me-4-OCF₃ CF₃ 2-Me-4-OCF₂H NO₂ 2-Me-4-OCF₂H SMe 2-Me-4-OCF₂H CF₃ 2-Me-4-OCH₂CF₃ NO₂ 2-Me-4-OCH₂CF₃ SMe 2-Me-4-OCH₂CF₃ CF₃ 2-Me-4-SCF₃ NO₂ 2-Me-4-SCF₃ SMe 2-Me-4-SCF₃ CF₃ 2-Me-4-SOCF₃ NO₂ 2-Me-4-SOCF₃ SMe 2-Me-4-SOCF₃ CF₃ 2-Me-4-SO₂CF₃ NO₂ 2-Me-4-SO₂CF₃ SMe 2-Me-4-SO₂CF₃ CF₃ 2-Me-4-SCF₂H NO₂ 2-Me-4-SCF₂H SMe 2-Me-4-SCF₂H CF₃ 2-Me-4-SOCF₂H NO₂ 2-Me-4-SOCF₂H SMe 2-Me-4-SOCF₂H CF₃ 2-Me-4-SO₂CF₂H NO₂ 2-Me-4-SO₂CF₂H SMe 2-Me-4-SO₂CF₂H

TABLE 5

R³ R⁴ R⁷ W X Y Z i-Pr Me CF₃ CMe N CH CH i-Pr Cl CF₃ CMe N CH CH i-Pr Br CF₃ CMe N CH CH i-Pr I CF₃ CMe N CH CH i-Pr F CF₃ CMe N CH CH i-Pr H CF₃ CMe N CH CH i-Pr Et CF₃ CMe N CH CH i-Pr Me CF₃ CMe CH N CH i-Pr Cl CF₃ CMe CH N CH i-Pr Br CF₃ CMe CH N CH i-Pr I CF₃ CMe CH N CH i-Pr F CF₃ CMe CH N CH i-Pr H CF₃ CMe CH N CH i-Pr Et CF₃ CMe CH N CH i-Pr Me CF₃ CMe CH CH N i-Pr Cl CF₃ CMe CH CH N i-Pr Br CF₃ CMe CH CH N i-Pr I CF₃ CMe CH CH N i-Pr F CF₃ CMe CH CH N i-Pr H CF₃ CMe CH CH N i-Pr Et CF₃ CMe CH CH N i-Pr Me CF₃ CMe N CH N i-Pr Cl CF₃ CMe N CH N i-Pr Br CF₃ CMe N CH N i-Pr I CF₃ CMe N CH N i-Pr F CF₃ CMe N CH N i-Pr H CF₃ CMe N CH N i-Pr Et CF₃ CMe N CH N t-Bu Me CF₃ CMe N CH CH t-Bu Cl CF₃ CMe N CH CH t-Bu Br CF₃ CMe N CH CH t-Bu I CF₃ CMe N CH CH t-Bu F CF₃ CMe N CH CH t-Bu H CF₃ CMe N CH CH t-Bu Et CF₃ CMe N CH CH t-Bu Me CF₃ CMe CH N CH t-Bu Cl CF₃ CMe CH N CH t-Bu Br CF₃ CMe CH N CH t-Bu I CF₃ CMe CH N CH t-Bu F CF₃ CMe CH N CH t-Bu H CF₃ CMe CH N CH t-Bu Et CF₃ CMe CH N CH t-Bu Me CF₃ CMe CH CH N t-Bu Cl CF₃ CMe CH CH N t-Bu Br CF₃ CMe CH CH N t-Bu I CF₃ CMe CH CH N t-Bu F CF₃ CMe CH CH N t-Bu H CF₃ CMe CH CH N t-Bu Et CF₃ CMe CH CH N i-Pr Me OCF₃ CMe N CH CH i-Pr Cl OCF₃ CMe N CH CH i-Pr Br OCF₃ CMe N CH CH i-Pr I OCF₃ CMe N CH CH i-Pr F OCF₃ CMe N CH CH i-Pr H OCF₃ CMe N CH CH i-Pr Et OCF₃ CMe N CH CH i-Pr Me CF₃ CH N CH CH i-Pr Cl CF₃ CH N CH CH i-Pr Br CF₃ CH N CH CH i-Pr I CF₃ CH N CH CH i-Pr F CF₃ CH N CH CH i-Pr H CF₃ CH N CH CH i-Pr Et CF₃ CH N CH CH i-Pr Me Cl CMe CH CH N i-Pr Cl Cl CMe CH CH N i-Pr Br Cl CMe CH CH N i-Pr I Cl CMe CH CH N i-Pr F Cl CMe CH CH N i-Pr H Cl CMe CH CH N i-Pr Et Cl CMe CH CH N

TABLE 6

R³ R⁴ R⁷ X Y Z i-Pr Me CF₃ CMe N CH i-Pr Cl CF₃ CMe N CH i-Pr Br CF₃ CMe N CH i-Pr I CF₃ CMe N CH i-Pr F CF₃ CMe N CH i-Pr H CF₃ CMe N CH i-Pr Et CF₃ CMe N CH i-Pr Me CF₃ CMe CH N i-Pr Cl CF₃ CMe CH N i-Pr Br CF₃ CMe CH N i-Pr I CF₃ CMe CH N i-Pr F CF₃ CMe CH N i-Pr H CF₃ CMe CH N i-Pr Et CF₃ CMe CH N i-Pr Me CF₃ CMe N N i-Pr Cl CF₃ CMe N N i-Pr Br CF₃ CMe N N i-Pr I CF₃ CMe N N i-Pr F CF₃ CMe N N i-Pr H CF₃ CMe N N i-Pr Et CF₃ CMe N N i-Pr Me CF₃ CEt CH N i-Pr Cl CF₃ CEt CH N i-Pr Br CF₃ CEt CH N i-Pr I CF₃ CEt CH N i-Pr F CF₃ CEt CH N i-Pr H CF₃ CEt CH N i-Pr Et CF₃ CEt CH N t-Bu Me CF₃ CMe N CH t-Bu Cl CF₃ CMe N CH t-Bu Br CF₃ CMe N CH t-Bu I CF₃ CMe N CH t-Bu F CF₃ CMe N CH t-Bu H CF₃ CMe N CH t-Bu Et CF₃ CMe N CH t-Bu Me CF₃ CMe CH N t-Bu Cl CF₃ CMe CH N t-Bu Br CF₃ CMe CH N t-Bu I CF₃ CMe CH N t-Bu F CF₃ CMe CH N t-Bu H CF₃ CMe CH N t-Bu Et CF₃ CMe CH N t-Bu Me CF₃ CMe N N t-Bu Cl CF₃ CMe N N t-Bu Br CF₃ CMe N N t-Bu I CF₃ CMe N N t-Bu F CF₃ CMe N N t-Bu H CF₃ CMe N N t-Bu Et CF₃ CMe N N i-Pr Me OCF₃ CMe CH N i-Pr Cl OCF₃ CMe CH N i-Pr Br OCF₃ CMe CH N i-Pr I OCF₃ CMe CH N i-Pr F OCF₃ CMe CH N i-Pr H OCF₃ CMe CH N i-Pr Et OCF₃ CMe CH N i-Pr Me CF₃ CH CH N i-Pr Cl CF₃ CH CH N i-Pr Br CF₃ CH CH N i-Pr I CF₃ CH CH N i-Pr F CF₃ CH CH N i-Pr H CF₃ CH CH N i-Pr Et CF₃ CH CH N i-Pr Me Cl CMe CH N i-Pr Cl Cl CMe CH N i-Pr Br Cl CMe CH N i-Pr I Cl CMe CH N i-Pr F Cl CMe CH N i-Pr H Cl CMe CH N i-Pr Et Cl CMe CH N

TABLE 7

R³ R⁴ Q X Y Z i-Pr Me S CCF₃ CH CH i-Pr Cl S CCF₃ CH CH i-Pr Br S CCF₃ CH CH i-Pr I S CCF₃ CH CH i-Pr F S CCF₃ CH CH i-Pr H S CCF₃ CH CH i-Pr Et S CCF₃ CH CH i-Pr Me S CCF₃ CMe CH i-Pr Cl S CCF₃ CMe CH i-Pr Br S CCF₃ CMe CH i-Pr I S CCF₃ CMe CH i-Pr F S CCF₃ CMe CH i-Pr H S CCF₃ CMe CH i-Pr Et S CCF₃ CMe CH t-Bu Me S CCF₃ CMe CH t-Bu Cl S CCF₃ CMe CH t-Bu Br S CCF₃ CMe CH t-Bu I S CCF₃ CMe CH t-Bu F S CCF₃ CMe CH t-Bu H S CCF₃ CMe CH t-Bu Et S CCF₃ CMe CH i-Pr Me S CCF₃ CMe N i-Pr Cl S CCF₃ CMe N i-Pr Br S CCF₃ CMe N i-Pr I S CCF₃ CMe N i-Pr F S CCF₃ CMe N i-Pr H S CCF₃ CMe N i-Pr Et S CCF₃ CMe N i-Pr Me S COCH₂CF₃ CMe N i-Pr Cl S COCH₂CF₃ CMe N i-Pr Br S COCH₂CF₃ CMe N i-Pr I S COCH₂CF₃ CMe N i-Pr F S COCH₂CF₃ CMe N i-Pr H S COCH₂CF₃ CMe N i-Pr Et S COCH₂CF₃ CMe N i-Pr Me S COCHF₂ CMe N i-Pr Cl S COCHF₂ CMe N i-Pr Br S COCHF₂ CMe N i-Pr I S COCHF₂ CMe N i-Pr F S COCHF₂ CMe N i-Pr H S COCHF₂ CMe N i-Pr Et S COCHF₂ CMe N i-Pr Me O CCF₃ CMe N i-Pr Cl O CCF₃ CMe N i-Pr Br O CCF₃ CMe N i-Pr I O CCF₃ CMe N i-Pr F O CCF₃ CMe N i-Pr H O CCF₃ CMe N i-Pr Et O CCF₃ CMe N i-Pr Me NMe N CH CCF₃ i-Pr Cl NMe N CH CCF₃ i-Pr Br NMe N CH CCF₃ i-Pr I NMe N CH CCF₃ i-Pr F NMe N CH CCF₃ i-Pr H NMe N CH CCF₃ i-Pr Et NMe N CH CCF₃ i-Pr Me NEt N CH CCF₃ i-Pr Cl NEt N CH CCF₃ i-Pr Br NEt N CH CCF₃ i-Pr I NEt N CH CCF₃ i-Pr F NEt N CH CCF₃ i-Pr H NEt N CH CCF₃ i-Pr Et NEt N CH CCF₃ i-Pr Me NMe N CH CC₂F₃ i-Pr Cl NMe N CH CC₂F₃ i-Pr Br NMe N CH CCF₃ i-Pr I NMe N CH CCF₃ i-Pr F NMe N CH CCF₃ i-Pr H NMe N CH CCF₃ i-Pr Et NMe N CH CCF₃ t-Bu Me NMe N CH CCF₃ t-Bu Cl NMe N CH CCF₃ t-Bu Br NMe N CH CCF₃ t-Bu I NMe N CH CCF₃ t-Bu F NMe N CH CCF₃ t-Bu H NMe N CH CCF₃ t-Bu Et NMe N CH CCF₃ i-Pr Me NMe CH N CCF₃ i-Pr Cl NMe CH N CCF₃ i-Pr Br NMe CH N CCF₃ i-Pr I NMe CH N CCF₃ i-Pr F NMe CH N CCF₃ i-Pr H NMe CH N CCF₃ i-Pr Et NMe CH N CCF₃ i-Pr Me NMe N N CCF₃ i-Pr Cl NMe N N CCF₃ i-Pr Br NMe N N CCF₃ i-Pr I NMe N N CCF₃ i-Pr F NMe N N CCF₃ i-Pr H NMe N N CCF₃ i-Pr Et NMe N N CCF₃

TABLE 8

R³ R⁴ Q X Y Z i-Pr Me NCHF₂ CMe N CH i-Pr Cl NCHF₂ CMe N CH i-Pr Br NCHF₂ CMe N CH i-Pr I NCHF₂ CMe N CH i-Pr F NCHF₂ CMe N CH i-Pr H NCHF₂ CMe N CH i-Pr Et NCHF₂ CMe N CH i-Pr Me NCHF₂ CH N CMe i-Pr Cl NCHF₂ CH N CMe i-Pr Br NCHF₂ CH N CMe i-Pr I NCHF₂ CH N CMe i-Pr F NCHF₂ CH N CMe i-Pr H NCHF₂ CH N CMe i-Pr Et NCHF₂ CH N CMe i-Pr Me NCF₂CHF₂ CMe N CH i-Pr Cl NCF₂CHF₂ CMe N CH i-Pr Br NCF₂CHF₂ CMe N CH i-Pr I NCF₂CHF₂ CMe N CH i-Pr F NCF₂CHF₂ CMe N CH i-Pr H NCF₂CHF₂ CMe N CH i-Pr Et NCF₂CHF₂ CMe N CH i-Pr Me NCF₂CHF₂ CH N CMe i-Pr Cl NCF₂CHF₂ CH N CMe i-Pr Br NCF₂CHF₂ CH N CMe i-Pr I NCF₂CHF₂ CH N CMe i-Pr F NCF₂CHF₂ CH N CMe i-Pr H NCF₂CHF₂ CH N CMe i-Pr Et NCF₂CHF₂ CH N CMe i-Pr Me NCH₂CF₃ CMe N CH i-Pr Cl NCH₂CF₃ CMe N CH i-Pr Br NCH₂CF₃ CMe N CH i-Pr I NCH₂CF₃ CMe N CH i-Pr F NCH₂CF₃ CMe N CH i-Pr H NCH₂CF₃ CMe N CH i-Pr Et NCH₂CF₃ CMe N CH i-Pr Me NCH₂CF₃ CH N CMe i-Pr Cl NCH₂CF₃ CH N CMe i-Pr Br NCH₂CF₃ CH N CMe i-Pr I NCH₂CF₃ CH N CMe i-Pr F NCH₂CF₃ CH N CMe i-Pr H NCH₂CF₃ CH N CMe i-Pr Et NCH₂CF₃ CH N CMe i-Pr Me NCF₂CHF₂ N CH CMe i-Pr Cl NCF₂CHF₂ N CH CMe i-Pr Br NCF₂CHF₂ N CH CMe i-Pr I NCF₂CHF₂ N CH CMe i-Pr F NCF₂CHF₂ N CH CMe i-Pr H NCF₂CHF₂ N CH CMe i-Pr Et NCF₂CHF₂ N CH CMe

TABLE 9

W X Y Z R³ R⁴ R⁷ R⁸ CH CH CH CH i-Pr Me CF₃ Me CH CH CH CH t-Bu Me CF₃ Me CH CH CH CH i-Pr Cl CF₃ Me CH CH CH CH t-Bu Cl CF₃ Me CH CH CH CH i-Pr Br CF₃ Me CH CH CH CH t-Bu Br CF₃ Me CH CH CH CH i-Pr Me Cl Me CH CH CH CH t-Bu Me Cl Me CH CH CH CH i-Pr Cl Cl Me CH CH CH CH t-Bu Cl Cl Me CH CH CH CH i-Pr Br Cl Me CH CH CH CH t-Bu Br Cl Me CH CH CH CH i-Pr Me Br Me CH CH CH CH t-Bu Me Br Me CH CH CH CH i-Pr Cl Br Me CH CH CH CH t-Bu Cl Br Me CH CH CH CH i-Pr Br Br Me CH CH CH CH t-Bu Br Br Me CH CH CH CH i-Pr Me CN Me CH CH CH CH t-Bu Me CN Me CH CH CH CH i-Pr Cl CN Me CH CH CH CH t-Bu Cl CN Me CH CH CH CH i-Pr Br CN Me CH CH CH CH t-Bu Br CN Me CH CH CH CH i-Pr Me CF₃ F CH CH CH CH t-Bu Me CF₃ F CH CH CH CH i-Pr Cl CF₃ F CH CH CH CH t-Bu Cl CF₃ F CH CH CH CH i-Pr Br CF₃ F CH CH CH CH t-Bu Br CF₃ F CH CH CH CH i-Pr Me Cl F CH CH CH CH t-Bu Me Cl F CH CH CH CH i-Pr Cl Cl F CH CH CH CH t-Bu Cl Cl F CH CH CH CH i-Pr Br Cl F CH CH CH CH t-Bu Br Cl F CH CH CH CH i-Pr Me Br F CH CH CH CH t-Bu Me Br F CH CH CH CH i-Pr Cl Br F CH CH CH CH t-Bu Cl Br F CH CH CH CH i-Pr Br Br F CH CH CH CH t-Bu Br Br F CH CH CH CH i-Pr Me CN F CH CH CH CH t-Bu Me CN F CH CH CH CH i-Pr Cl CN F CH CH CH CH t-Bu Cl CN F CH CH CH CH i-Pr Br CN F CH CH CH CH i-Pr Me Br Br CH CH CH CH t-Bu Me Br Br CH CH CH CH i-Pr Cl Br Br CH CH CH CH t-Bu Cl Br Br CH CH CH CH i-Pr Br Br Br CH CH CH CH t-Bu Br Br Br CH CH CH CH i-Pr Me CN Br CH CH CH CH t-Bu Me CN Br CH CH CH CH i-Pr Cl CN Br CH CH CH CH t-Bu Cl CN Br CH CH CH CH i-Pr Br CN Br CH CH CH CH t-Bu Br CN Br CH CH CH CH i-Pr Me CF₃ CN CH CH CH CH t-Bu Me CF₃ CN CH CH CH CH i-Pr Cl CF₃ CN CH CH CH CH t-Bu Cl CF₃ CN CH CH CH CH i-Pr Br CF₃ CN CH CH CH CH t-Bu Br CF₃ CN CH CH CH CH i-Pr Me Cl CN CH CH CH CH t-Bu Me Cl CN CH CH CH CH i-Pr Cl Cl CN CH CH CH CH t-Bu Cl Cl CN CH CH CH CH i-Pr Br Cl CN CH CH CH CH t-Bu Br Cl CN CH CH CH CH i-Pr Me Br CN CH CH CH CH t-Bu Me Br CN CH CH CH CH i-Pr Cl Br CN CH CH CH CH t-Bu Cl Br CN CH CH CH CH i-Pr Br Br CN CH CH CH CH t-Bu Br Br CN CH CH CH CH i-Pr Me CN CN CH CH CH CH t-Bu Me CN CN CH CH CH CH i-Pr Cl CN CN CH CH CH CH t-Bu Cl CN CN CH CH CH CH i-Pr Br CN CN CH CH CH CH t-Bu Br CN CN CH CH CH N i-Pr Me CF₃ Me CH CH CH CH t-Bu Br CN F CH CH CH CH i-Pr Me CF₃ Cl CH CH CH CH t-Bu Me CF₃ Cl CH CH CH CH i-Pr Cl CF₃ Cl CH CH CH CH t-Bu Cl CF₃ Cl CH CH CH CH i-Pr Br CF₃ Cl CH CH CH CH t-Bu Br CF₃ Cl CH CH CH CH i-Pr Me Cl Cl CH CH CH CH t-Bu Me Cl Cl CH CH CH CH i-Pr Cl Cl Cl CH CH CH CH t-Bu Cl Cl Cl CH CH CH CH i-Pr Br Cl Cl CH CH CH CH t-Bu Br Cl Cl CH CH CH CH i-Pr Me Br Cl CH CH CH CH t-Bu Me Br Cl CH CH CH CH i-Pr Cl Br Cl CH CH CH CH t-Bu Cl Br Cl CH CH CH CH i-Pr Br Br Cl CH CH CH CH t-Bu Br Br Cl CH CH CH CH i-Pr Me CN Cl CH CH CH CH t-Bu Me CN Cl CH CH CH CH i-Pr Cl CN Cl CH CH CH CH t-Bu Cl CN Cl CH CH CH CH i-Pr Br CN Cl CH CH CH CH t-Bu Br CN Cl CH CH CH CH i-Pr Me CF₃ Br CH CH CH CH t-Bu Me CF₃ Br CH CH CH CH i-Pr Cl CF₃ Br CH CH CH CH t-Bu Cl CF₃ Br CH CH CH CH i-Pr Br CF₃ Br CH CH CH CH t-Bu Br CF₃ Br CH CH CH CH i-Pr Me Cl Br CH CH CH CH t-Bu Me Cl Br CH CH CH CH i-Pr Cl Cl Br CH CH CH CH t-Bu Cl Cl Br CH CH CH CH i-Pr Br Cl Br CH CH CH CH t-Bu Br Cl Br CH CH CH N t-Bu Me CF₃ Me CH CH CH N i-Pr Cl CF₃ Me CH CH CH N t-Bu Cl CF₃ Me CH CH CH N i-Pr Br CF₃ Me CH CH CH N t-Bu Br CF₃ Me CH CH CH N i-Pr Me Cl Me CH CH CH N t-Bu Me Cl Me CH CH CH N i-Pr Cl Cl Me CH CH CH N t-Bu Cl Cl Me CH CH CH N i-Pr Br Cl Me CH CH CH N t-Bu Br Cl Me CH CH CH N i-Pr Me Br Me CH CH CH N t-Bu Me Br Me CH CH CH N i-Pr Cl Br Me CH CH CH N t-Bu Cl Br Me CH CH CH N i-Pr Br Br Me CH CH CH N t-Bu Br Br Me CH CH CH N i-Pr Me CN Me CH CH CH N t-Bu Me CN Me CH CH CH N i-Pr Cl CN Me CH CH CH N t-Bu Cl CN Me CH CH CH N i-Pr Br CN Me CH CH CH N t-Bu Br CN Me CH CH CH N i-Pr Me CF₃ F CH CH CH N t-Bu Me CF₃ F CH CH CH N i-Pr Cl CF₃ F CH CH CH N t-Bu Cl CF₃ F CH CH CH N i-Pr Br CF₃ F CH CH CH N t-Bu Br CF₃ F CH CH CH N i-Pr Me Cl F CH CH CH N t-Bu Me Cl F CH CH CH N i-Pr Cl Cl F CH CH CH N t-Bu Cl Cl F CH CH CH N i-Pr Br Cl F CH CH CH N t-Bu Br Cl F CH CH CH N i-Pr Me Br F CH CH CH N t-Bu Me Br F CH CH CH N i-Pr Cl Br F CH CH CH N t-Bu Cl Br F CH CH CH N i-Pr Br Br F CH CH CH N t-Bu Br Br F CH CH CH N i-Pr Me CN F CH CH CH N t-Bu Me CN F CH CH CH N i-Pr Cl CN F CH CH CH N t-Bu Cl CN F CH CH CH N i-Pr Br CN F CH CH CH N t-Bu Br CN F CH CH CH N i-Pr Me CF₃ Cl CH CH CH N t-Bu Me CF₃ Cl CH CH CH N i-Pr Cl CF₃ Cl CH CH CH N t-Bu Cl CF₃ Cl CH CH CH N i-Pr Br CF₃ Cl CH CH CH N t-Bu Br CF₃ Cl CH CH CH N i-Pr Me Cl Cl CH CH CH N t-Bu Me Cl Cl CH CH CH N i-Pr Cl Cl Cl CH CH CH N t-Bu Cl Cl Cl CH CH CH N i-Pr Br Cl Cl CH CH CH N t-Bu Br Cl Cl CH CH CH N i-Pr Me Br Cl CH CH CH N t-Bu Me Br Cl CH CH CH N i-Pr Cl Br Cl CH CH CH N t-Bu Cl Br Cl CH CH CH N i-Pr Br Br Cl CH CH CH N t-Bu Br Br Cl CH CH CH N i-Pr Me CN Cl CH CH CH N t-Bu Me CN Cl CH CH CH N i-Pr Cl CN Cl CH CH CH N t-Bu Cl CN Cl CH CH CH N i-Pr Br CN Cl CH CH CH N t-Bu Br CN Cl CH CH CH N i-Pr Me CF₃ Br CH CH CH N t-Bu Me CF₃ Br CH CH CH N i-Pr Cl CF₃ Br CH CH CH N t-Bu Cl CF₃ Br CH CH CH N i-Pr Br CF₃ Br CH CH CH N t-Bu Br CF₃ Br CH CH CH N i-Pr Me Cl Br CH CH CH N t-Bu Me Cl Br CH CH CH N i-Pr Cl Cl Br CH CH CH N t-Bu Cl Cl Br CH CH CH N i-Pr Br Cl Br CH CH CH N t-Bu Br Cl Br CH CH CH N i-Pr Me Br Br CH CH CH N t-Bu Me Br Br CH CH CH N i-Pr Cl Br Br CH CH CH N t-Bu Cl Br Br CH CH CH N i-Pr Br Br Br CH CH CH N t-Bu Br Br Br CH CH CH N i-Pr Me CN Br CH CH CH N t-Bu Me CN Br CH CH CH N i-Pr Cl CN Br CH CH CH N t-Bu Cl CN Br CH CH CH N i-Pr Br CN Br CH CH CH N t-Bu Br CN Br CH CH CH N i-Pr Me CF₃ CN CH CH CH N t-Bu Me CF₃ CN CH CH CH N i-Pr Cl CF₃ CN CH CH CH N t-Bu Cl CF₃ CN CH CH CH N i-Pr Br CF₃ CN CH CH CH N t-Bu Br CF₃ CN CH CH CH N i-Pr Me Cl CN CH CH CH N t-Bu Me Cl CN CH CH CH N i-Pr Cl Cl CN CH CH CH N t-Bu Cl Cl CN CH CH CH N i-Pr Br Cl CN CH CH CH N t-Bu Br Cl CN CH CH CH N i-Pr Me Br CN CH CH CH N t-Bu Me Br CN CH CH CH N i-Pr Cl Br CN CH CH CH N t-Bu Cl Br CN CH CH CH N i-Pr Br Br CN CH CH CH N t-Bu Br Br CN CH CH CH N i-Pr Me CN CN CH CH CH N t-Bu Me CN CN CH CH CH N i-Pr Cl CN CN CH CH CH N t-Bu Cl CN CN CH CH CH N i-Pr Br CN CN CH CH CH N t-Bu Br CN CN CH CH CH CH Me Me CF₃ F CH CH CH CH Et Me CF₃ F CH CH CH CH CH(CH₃)CH₂OCH₃ Me CF₃ F CH CH CH CH CH(CH₃)CH₂SCH₃ Me CF₃ F CH CH CH CH propargyl Me CF₃ F CH CH CH CH Me Me CF₃ Cl CH CH CH CH Et Me CF₃ Cl CH CH CH CH CH(CH₃)CH₂OCH₃ Me CF₃ Cl CH CH CH CH CH(CH₃)CH₂SCH₃ Me CF₃ Cl CH CH CH CH propargyl Me CF₃ Cl CH CH CH CH Me Me Br F CH CH CH CH Et Me Br F CH CH CH CH CH(CH₃)CH₂OCH₃ Me Br F CH CH CH CH CH(CH₃)CH₂SCH₃ Me Br F CH CH CH CH propargyl Me Br F CH CH CH CH Me Me Br Cl CH CH CH CH Et Me Br Cl CH CH CH CH CH(CH₃)CH₂OCH₃ Me Br Cl CH CH CH CH CH(CH₃)CH₂SCH₃ Me Br Cl CH CH CH CH propargyl Me Br Cl CH CH CH CH Me Cl CF₃ F CH CH CH CH Et Cl CF₃ F CH CH CH CH CH(CH₃)CH₂OCH₃ Cl CF₃ F CH CH CH CH CH(CH₃)CH₂SCH₃ Cl CF₃ F CH CH CH CH propargyl Cl CF₃ F CH CH CH CH Me Cl CF₃ Cl CH CH CH CH Et Cl CF₃ Cl CH CH CH CH CH(CH₃)CH₂OCH₃ Cl CF₃ Cl CH CH CH CH CH(CH₃)CH₂SCH₃ Cl CF₃ Cl CH CH CH CH propargyl Cl CF₃ Cl CH CH CH CH Me Cl Br F CH CH CH CH Et Cl Br F CH CH CH CH CH(CH₃)CH₂OCH₃ Cl Br F CH CH CH CH CH(CH₃)CH₂SCH₃ Cl Br F CH CH CH CH propargyl Cl Br F CH CH CH CH Me Cl Br Cl CH CH CH CH Et Cl Br Cl CH CH CH CH CH(CH₃)CH₂OCH₃ Cl Br Cl CH CH CH CH CH(CH₃)CH₂SCH₃ Cl Br Cl CH CH CH CH propargyl Cl Br Cl CH CH CH N Me Me CF₃ F CH CH CH N Et Me CF₃ F CH CH CH N CH(CH₃)CH₂OCH₃ Me CF₃ F CH CH CH N CH(CH₃)CH₂SCH₃ Me CF₃ F CH CH CH N propargyl Me CF₃ F CH CH CH N Me Me CF₃ Cl CH CH CH N Et Me CF₃ Cl CH CH CH N CH(CH₃)CH₂OCH₃ Me CF₃ Cl CH CH CH N CH(CH₃)CH₂SCH₃ Me CF₃ Cl CH CH CH N propargyl Me CF₃ Cl CH CH CH N Me Me Br F CH CH CH N Et Me Br F CH CH CH N CH(CH₃)CH₂OCH₃ Me Br F CH CH CH N CH(CH₃)CH₂SCH₃ Me Br F CH CH CH N propargyl Me Br F CH CH CH N Me Me Br Cl CH CH CH N Et Me Br Cl CH CH CH N CH(CH₃)CH₂OCH₃ Me Br Cl CH CH CH N CH(CH₃)CH₂SCH₃ Me Br Cl CH CH CH N propargyl Me Br Cl CH CH CH N Me Cl CF₃ F CH CH CH N Et Cl CF₃ F CH CH CH N CH(CH₃)CH₂OCH₃ Cl CF₃ F CH CH CH N CH(CH₃)CH₂SCH₃ Cl CF₃ F CH CH CH N propargyl Cl CF₃ F CH CH CH N Me Cl CF₃ Cl CH CH CH N Et Cl CF₃ Cl CH CH CH N CH(CH₃)CH₂OCH₃ Cl CF₃ Cl CH CH CH N CH(CH₃)CH₂SCH₃ Cl CF₃ Cl CH CH CH N propargyl Cl CF₃ Cl CH CH CH N Me Cl Br F CH CH CH N Et Cl Br F CH CH CH N CH(CH₃)CH₂OCH₃ Cl Br F CH CH CH N CH(CH₃)CH₂SCH₃ Cl Br F CH CH CH N Propargyl Cl Br F CH CH CH N Me Cl Br Cl CH CH CH N Et Cl Br Cl CH CH CH N CH(CH₃)CH₂OCH₃ Cl Br Cl CH CH CH N CH(CH₃)CH₂SCH₃ Cl Br Cl CH CH CH N propargyl Cl Br Cl C—Cl CH CH CH i-Pr Me CF₃ Cl C—F CH CH CH i-Pr Me CF₃ F CH CH CH CH i-Pr Me CF₃ acetylene CH CH CH CH i-Pr Me CF₃ I CH CH CH CH i-Pr Me CF₃ SO₂Me C—Cl CH CH CH i-Pr Cl CF₃ Cl C—F CH CH CH i-Pr Cl CF₃ F CH CH CH CH i-Pr Cl CF₃ acetylene CH CH CH CH i-Pr Cl CF₃ I CH CH CH CH i-Pr Cl CF₃ SO₂Me C—Cl CH CH CH i-Pr Me Br Cl C—F CH CH CH i-Pr Me Br F CH CH CH CH i-Pr Me Br acetylene CH CH CH CH i-Pr Me Br I CH CH CH CH i-Pr Me Br SO₂Me C—Cl CH CH CH i-Pr Cl Br Cl C—F CH CH CH i-Pr Cl Br F CH CH CH CH i-Pr Cl Br acetylene CH CH CH CH i-Pr Cl Br I CH CH CH CH i-Pr Cl Br SO₂Me C—Cl CH CH N i-Pr Me CF₃ Cl C—F CH CH N i-Pr Me CF₃ F CH CH CH N i-Pr Me CF₃ acetylene CH CH CH N i-Pr Me CF₃ I CH CH CH N i-Pr Me CF₃ SO₂Me C—Cl CH CH N i-Pr Cl CF₃ Cl C—F CH CH N i-Pr Cl CF₃ F CH CH CH N i-Pr Cl CF₃ acetylene CH CH CH N i-Pr Cl CF₃ I CH CH CH N i-Pr Cl CF₃ SO₂Me C—Cl CH CH N i-Pr Me Br Cl C—F CH CH N i-Pr Me Br F CH CH CH N i-Pr Me Br acetylene CH CH CH N i-Pr Me Br I CH CH CH N i-Pr Me Br SO₂Me C—Cl CH CH N i-Pr Cl Br Cl C—F CH CH N i-Pr Cl Br F CH CH CH N i-Pr Cl Br acetylene CH CH CH N i-Pr Cl Br I CH CH CH N i-Pr Cl Br SO₂Me CH N CH N i-Pr Me CF₃ H CH N CH N i-Pr Me CF₃ Me CH N CH N i-Pr Me CF₃ Cl CH N CH N i-Pr Cl CF₃ H CH N CH N i-Pr Cl CF₃ Me CH N CH N i-Pr Cl CF₃ Cl CH N CH N i-Pr Me CN H CH N CH N i-Pr Me CN Me CH N CH N i-Pr Me CN Cl CH N CH N i-Pr Cl CN H CH N CH N i-Pr Cl CN Me CH N CH N i-Pr Cl CN Cl CH N CH N i-Pr Me Br H CH N CH N i-Pr Me Br Me CH N CH N i-Pr Me Br Cl CH N CH N i-Pr Cl Br H CH N CH N i-Pr Cl Br Me CH N CH N i-Pr Cl Br Cl CH N CH N t-Bu Me CF₃ H CH N CH N t-Bu Me CF₃ Me CH N CH N t-Bu Me CF₃ Cl CH N CH N t-Bu Cl CF₃ H CH N CH N t-Bu Cl CF₃ Me CH N CH N t-Bu Cl CF₃ Cl CH N CH N t-Bu Me CN H CH N CH N t-Bu Me CN Me CH N CH N t-Bu Me CN Cl CH N CH N t-Bu Cl CN H CH N CH N t-Bu Cl CN Me CH N CH N t-Bu Cl CN Cl CH N CH N t-Bu Me Br H CH N CH N t-Bu Me Br Me CH N CH N t-Bu Me Br Cl CH N CH N t-Bu Cl Br H CH N CH N t-Bu Cl Br Me CH N CH N t-Bu Cl Br Cl CH CH N N i-Pr Me CF₃ H CH CH N N i-Pr Me CF₃ Me CH CH N N i-Pr Me CF₃ Cl CH CH N N i-Pr Cl CF₃ H CH CH N N i-Pr Cl CF₃ Me CH CH N N i-Pr Cl CF₃ Cl CH CH N N i-Pr Me CN H CH CH N N i-Pr Me CN Me CH CH N N i-Pr Me CN Cl CH CH N N i-Pr Cl CN H CH CH N N i-Pr Cl CN Me CH CH N N i-Pr Cl CN Cl CH CH N N i-Pr Me Br H CH CH N N i-Pr Me Br Me CH CH N N i-Pr Me Br Cl CH CH N N i-Pr Cl Br H CH CH N N i-Pr Cl Br Me CH CH N N i-Pr Cl Br Cl CH CH N N i-Pr Me CF₃ H CH CH N N i-Pr Me CF₃ Me CH CH N N i-Pr Me CF₃ Cl CH CH N N i-Pr Cl CF₃ H CH CH N N i-Pr Cl CF₃ Me CH CH N N i-Pr Cl CF₃ Cl CH CH N N i-Pr Me CN H CH CH N N i-Pr Me CN Me CH CH N N i-Pr Me CN Cl CH CH N N i-Pr Cl CN H CH CH N N i-Pr Cl CN Me CH CH N N i-Pr Cl CN Cl CH CH N N i-Pr Me Br H CH CH N N i-Pr Me Br Me CH CH N N i-Pr Me Br Cl CH CH N N i-Pr Cl Br H CH CH N N i-Pr Cl Br Me CH CH N N i-Pr Cl Br Cl

TABLE 10

R⁴ R⁷ R³ R⁸ R⁹ R¹⁰ Me CF₃ i-Pr Me H H Me CF₃ i-Pr Me H Me Me CF₃ i-Pr Me Cl H Me CF₃ i-Pr Me Cl Me Me CF₃ i-Pr Me Me Me Cl CF₃ i-Pr Me H H Cl CF₃ i-Pr Me H Me Cl CF₃ i-Pr Me Cl H Cl CF₃ i-Pr Me Cl Me Cl CF₃ i-Pr Me Me Me Me CF₃ t-Bu Me H H Me CF₃ t-Bu Me H Me Me CF₃ t-Bu Me Cl H Me CF₃ t-Bu Me Cl Me Me CF₃ t-Bu Me Me Me Cl CF₃ t-Bu Me H H Cl CF₃ t-Bu Me H Me Cl CF₃ t-Bu Me Cl H Cl CF₃ t-Bu Me Cl Me Cl CF₃ t-Bu Me Me Me

TABLE 11

R⁴ R⁷ R³ R⁸ R⁹ R¹⁰ Me CF₃ i-Pr Me H Me Me CF₃ i-Pr Me Me Me Me CF₃ i-Pr Cl H Me Me CF₃ i-Pr Cl Me Me Cl CF₃ i-Pr Me H Me Cl CF₃ i-Pr Me Me Me Cl CF₃ i-Pr Cl H Me Cl CF₃ i-Pr Cl Me Me Me CF₃ t-Bu Me H Me Me CF₃ t-Bu Me Me Me Me CF₃ t-Bu Cl H Me Me CF₃ t-Bu Cl Me Me Cl CF₃ t-Bu Me H Me Cl CF₃ t-Bu Me Me Me Cl CF₃ t-Bu Cl H Me Cl CF₃ t-Bu Cl Me Me

TABLE 12

W X Y Z R³ R⁴ R⁷ R⁸ CH CH CH CH Et Me CF₃ Cl CH CH CH CH i-Pr Me CF₃ Cl CH CH CH CH t-Bu Me CF₃ Cl CH CH CH CH Et Me CF₃ Br CH CH CH CH i-Pr Me CF₃ Br CH CH CH CH t-Bu Me CF₃ Br CH CH CH CH Et Me CF₃ I CH CH CH CH i-Pr Me CF₃ I CH CH CH CH t-Bu Me CF₃ I CH CH CH CH Et Me CF₃ F CH CH CH CH i-Pr Me CF₃ F CH CH CH CH t-Bu Me CF₃ F CH CH CH CH Et Me CF₃ Me CH CH CH CH i-Pr Me CF₃ Me CH CH CH CH t-Bu Me CF₃ Me CH CH CH CH Et Me CF₃ CF₃ CH CH CH CH i-Pr Me CF₃ CF₃ CH CH CH CH t-Bu Me CF₃ CF₃ CH CH CH CH Et Me CF₃ OMe CH CH CH CH i-Pr Me CF₃ OMe CH CH CH CH t-Bu Me CF₃ OMe CH CH CH CH Et Me CF₃ CN CH CH CH CH i-Pr Me CF₃ CN CH CH CH CH t-Bu Me CF₃ CN CH CH CH CH Et Cl CF₃ Cl CH CH CH CH i-Pr Cl CF₃ Cl CH CH CH CH t-Bu Cl CF₃ Cl CH CH CH CH Et Cl CF₃ Br CH CH CH CH i-Pr Cl CF₃ Br CH CH CH CH t-Bu Cl CF₃ Br CH CH CH CH Et Cl CF₃ I CH CH CH CH i-Pr Cl CF₃ I CH CH CH CH t-Bu Cl CF₃ I CH CH CH CH Et Cl CF₃ F CH CH CH CH i-Pr Cl CF₃ F CH CH CH CH t-Bu Cl CF₃ F CH CH CH CH Et Cl CF₃ Me CH CH CH CH i-Pr Cl CF₃ Me CH CH CH CH t-Bu Cl CF₃ Me CH CH CH CH Et Cl CF₃ CF₃ CH CH CH CH i-Pr Cl CF₃ CF₃ CH CH CH CH t-Bu Cl CF₃ CF₃ CH CH CH CH Et Cl CF₃ OMe CH CH CH CH i-Pr Cl CF₃ OMe CH CH CH CH t-Bu Cl CF₃ OMe CH CH CH CH Et Cl CF₃ CN CH CH CH CH i-Pr Cl CF₃ CN CH CH CH CH t-Bu Cl CF₃ CN CH CH CH N Et Me CF₃ Cl CH CH CH N i-Pr Me CF₃ Cl CH CH CH N t-Bu Me CF₃ Cl CH CH CH N Et Me CF₃ Br CH CH CH N i-Pr Me CF₃ Br CH CH CH N t-Bu Me CF₃ Br CH CH CH N Et Me CF₃ I CH CH CH N i-Pr Me CF₃ I CH CH CH N t-Bu Me CF₃ I CH CH CH N Et Me CF₃ F CH CH CH N i-Pr Me CF₃ F CH CH CH N t-Bu Me CF₃ F CH CH CH N Et Me CF₃ Me CH CH CH N i-Pr Me CF₃ Me CH CH CH N t-Bu Me CF₃ Me CH CH CH N Et Me CF₃ CF₃ CH CH CH N i-Pr Me CF₃ CF₃ CH CH CH N t-Bu Me CF₃ CF₃ CH CH CH N Et Me CF₃ OMe CH CH CH N i-Pr Me CF₃ OMe CH CH CH N t-Bu Me CF₃ OMe CH CH CH N Et Me CF₃ CN CH CH CH N i-Pr Me CF₃ CN CH CH CH N t-Bu Me CF₃ CN CH CH CH N Et Cl CF₃ Cl CH CH CH N i-Pr Cl CF₃ Cl CH CH CH N t-Bu Cl CF₃ Cl CH CH CH N Et Cl CF₃ Br CH CH CH N i-Pr Cl CF₃ Br CH CH CH N t-Bu Cl CF₃ Br CH CH CH N Et Cl CF₃ I CH CH CH N i-Pr Cl CF₃ I CH CH CH N t-Bu Cl CF₃ I CH CH CH N Et Cl CF₃ F CH CH CH N i-Pr Cl CF₃ F CH CH CH N t-Bu Cl CF₃ F CH CH CH N Et Cl CF₃ Me CH CH CH N i-Pr Cl CF₃ Me CH CH CH N t-Bu Cl CF₃ Me CH CH CH N Et Cl CF₃ CF₃ CH CH CH N i-Pr Cl CF₃ CF₃ CH CH CH N t-Bu Cl CF₃ CF₃ CH CH CH N Et Cl CF₃ OMe CH CH CH N i-Pr Cl CF₃ OMe CH CH CH N t-Bu Cl CF₃ OMe CH CH CH N Et Cl CF₃ CN CH CH CH N i-Pr Cl CF₃ CN CH CH CH N t-Bu Cl CF₃ CN CH CH N CH Et Me CF₃ Cl CH CH N CH i-Pr Me CF₃ Cl CH CH N CH t-Bu Me CF₃ Cl CH CH N CH Et Me CF₃ Br CH CH N CH i-Pr Me CF₃ Br CH CH N CH t-Bu Me CF₃ Br CH CH N CH Et Me CF₃ I CH CH N CH i-Pr Me CF₃ I CH CH N CH t-Bu Me CF₃ I CH CH N CH Et Me CF₃ F CH CH N CH i-Pr Me CF₃ F CH CH N CH t-Bu Me CF₃ F CH CH N CH Et Me CF₃ Me CH CH N CH i-Pr Me CF₃ Me CH CH N CH t-Bu Me CF₃ Me CH CH N CH Et Me CF₃ CF₃ CH CH N CH i-Pr Me CF₃ CF₃ CH CH N CH t-Bu Me CF₃ CF₃ CH CH N CH Et Me CF₃ OMe CH CH N CH i-Pr Me CF₃ OMe CH CH N CH t-Bu Me CF₃ OMe CH CH N CH Et Me CF₃ CN CH CH N CH i-Pr Me CF₃ CN CH CH N CH t-Bu Me CF₃ CN CH CH N CH Et Cl CF₃ Cl CH CH N CH i-Pr Cl CF₃ Cl CH CH N CH t-Bu Cl CF₃ Cl CH CH N CH Et Cl CF₃ Br CH CH N CH i-Pr Cl CF₃ Br CH CH N CH t-Bu Cl CF₃ Br CH CH N CH Et Cl CF₃ I CH CH N CH i-Pr Cl CF₃ I CH CH N CH t-Bu Cl CF₃ I CH CH N CH Et Cl CF₃ F CH CH N CH i-Pr Cl CF₃ F CH CH N CH t-Bu Cl CF₃ F CH CH N CH Et Cl CF₃ Me CH CH N CH i-Pr Cl CF₃ Me CH CH N CH t-Bu Cl CF₃ Me CH CH N CH Et Cl CF₃ CF₃ CH CH N CH i-Pr Cl CF₃ CF₃ CH CH N CH t-Bu Cl CF₃ CF₃ CH CH N CH Et Cl CF₃ OMe CH CH N CH i-Pr Cl CF₃ OMe CH CH N CH t-Bu Cl CF₃ OMe CH CH N CH Et Cl CF₃ CN CH CH N CH i-Pr Cl CF₃ CN CH CH N CH t-Bu Cl CF₃ CN CH N CH CH Et Me CF₃ Cl CH N CH CH i-Pr Me CF₃ Cl CH N CH CH t-Bu Me CF₃ Cl CH N CH CH Et Me CF₃ Br CH N CH CH i-Pr Me CF₃ Br CH N CH CH t-Bu Me CF₃ Br CH N CH CH Et Me CF₃ I CH N CH CH i-Pr Me CF₃ I CH N CH CH t-Bu Me CF₃ I CH N CH CH Et Me CF₃ F CH N CH CH i-Pr Me CF₃ F CH N CH CH t-Bu Me CF₃ F CH N CH CH Et Me CF₃ Me CH N CH CH i-Pr Me CF₃ Me CH N CH CH t-Bu Me CF₃ Me CH N CH CH Et Me CF₃ CF₃ CH N CH CH i-Pr Me CF₃ CF₃ CH N CH CH t-Bu Me CF₃ CF₃ CH N CH CH Et Me CF₃ OMe CH N CH CH i-Pr Me CF₃ OMe CH N CH CH t-Bu Me CF₃ OMe CH N CH CH Et Me CF₃ CN CH N CH CH i-Pr Me CF₃ CN CH N CH CH t-Bu Me CF₃ CN CH N CH CH Et Cl CF₃ Cl CH N CH CH i-Pr Cl CF₃ Cl CH N CH CH t-Bu Cl CF₃ Cl CH N CH CH Et Cl CF₃ Br CH N CH CH i-Pr Cl CF₃ Br CH N CH CH t-Bu Cl CF₃ Br CH N CH CH Et Cl CF₃ I CH N CH CH i-Pr Cl CF₃ I CH N CH CH t-Bu Cl CF₃ I CH N CH CH Et Cl CF₃ F CH N CH CH i-Pr Cl CF₃ F CH N CH CH t-Bu Cl CF₃ F CH N CH CH Et Cl CF₃ Me CH N CH CH i-Pr Cl CF₃ Me CH N CH CH t-Bu Cl CF₃ Me CH N CH CH Et Cl CF₃ CF₃ CH N CH CH i-Pr Cl CF₃ CF₃ CH N CH CH t-Bu Cl CF₃ CF₃ CH N CH CH Et Cl CF₃ OMe CH N CH CH i-Pr Cl CF₃ OMe CH N CH CH t-Bu Cl CF₃ OMe CH N CH CH Et Cl CF₃ CN CH N CH CH i-Pr Cl CF₃ CN CH N CH CH t-Bu Cl CF₃ CN N CH CH CH Et Me CF₃ Cl N CH CH CH i-Pr Me CF₃ Cl N CH CH CH t-Bu Me CF₃ Cl N CH CH CH Et Me CF₃ Br N CH CH CH i-Pr Me CF₃ Br N CH CH CH t-Bu Me CF₃ Br N CH CH CH Et Me CF₃ I N CH CH CH i-Pr Me CF₃ I N CH CH CH t-Bu Me CF₃ I N CH CH CH Et Me CF₃ F N CH CH CH i-Pr Me CF₃ F N CH CH CH t-Bu Me CF₃ F N CH CH CH Et Me CF₃ Me N CH CH CH i-Pr Me CF₃ Me N CH CH CH t-Bu Me CF₃ Me N CH CH CH Et Me CF₃ CF₃ N CH CH CH i-Pr Me CF₃ CF₃ N CH CH CH t-Bu Me CF₃ CF₃ N CH CH CH Et Me CF₃ OMe N CH CH CH i-Pr Me CF₃ OMe N CH CH CH t-Bu Me CF₃ OMe N CH CH CH Et Me CF₃ CN N CH CH CH i-Pr Me CF₃ CN N CH CH CH t-Bu Me CF₃ CN N CH CH CH Et Cl CF₃ Cl N CH CH CH i-Pr Cl CF₃ Cl N CH CH CH t-Bu Cl CF₃ Cl N CH CH CH Et Cl CF₃ Br N CH CH CH i-Pr Cl CF₃ Br N CH CH CH t-Bu Cl CF₃ Br N CH CH CH Et Cl CF₃ I N CH CH CH i-Pr Cl CF₃ I N CH CH CH t-Bu Cl CF₃ I N CH CH CH Et Cl CF₃ F N CH CH CH i-Pr Cl CF₃ F N CH CH CH t-Bu Cl CF₃ F N CH CH CH Et Cl CF₃ Me N CH CH CH i-Pr Cl CF₃ Me N CH CH CH t-Bu Cl CF₃ Me N CH CH CH Et Cl CF₃ CF₃ N CH CH CH i-Pr Cl CF₃ CF₃ N CH CH CH t-Bu Cl CF₃ CF₃ N CH CH CH Et Cl CF₃ OMe N CH CH CH i-Pr Cl CF₃ OMe N CH CH CH t-Bu Cl CF₃ OMe N CH CH CH Et Cl CF₃ CN N CH CH CH i-Pr Cl CF₃ CN N CH CH CH t-Bu Cl CF₃ CN CH N CH N Et Me CF₃ Cl CH N CH N i-Pr Me CF₃ Cl CH N CH N t-Bu Me CF₃ Cl CH N CH N Et Me CF₃ Br CH N CH N i-Pr Me CF₃ Br CH N CH N t-Bu Me CF₃ Br CH N CH N Et Me CF₃ I CH N CH N i-Fr Me CF₃ I CH N CH N t-Bu Me CF₃ I CH N CH N Et Me CF₃ F CH N CH N i-Pr Me CF₃ F CH N CH N t-Bu Me CF₃ F CH N CH N Et Me CF₃ Me CH N CH N i-Pr Me CF₃ Me CH N CH N t-Bu Me CF₃ Me CH N CH N Et Me CF₃ CF₃ CH N CH N i-Pr Me CF₃ CF₃ CH N CH N t-Bu Me CF₃ CF₃ CH N CH N Et Me CF₃ OMe CH N CH N i-Pr Me CF₃ OMe CH N CH N t-Bu Me CF₃ OMe CH N CH N Et Me CF₃ CN CH N CH N i-Pr Me CF₃ CN CH N CH N t-Bu Me CF₃ CN CH N CH N Et Cl CF₃ Cl CH N CH N i-Pr Cl CF₃ Cl CH N CH N t-Bu Cl CF₃ Cl CH N CH N Et Cl CF₃ Br CH N CH N i-Pr Cl CF₃ Br CH N CH N t-Bu Cl CF₃ Br CH N CH N Et Cl CF₃ I CH N CH N i-Pr Cl CF₃ I CH N CH N t-Bu Cl CF₃ I CH N CH N Et Cl CF₃ F CH N CH N i-Pr Cl CF₃ F CH N CH N t-Bu Cl CF₃ F CH N CH N Et Cl CF₃ Me CH N CH N i-Pr Cl CF₃ Me CH N CH N t-Bu Cl CF₃ Me CH N CH N Et Cl CF₃ CF₃ CH N CH N i-Pr Cl CF₃ CF₃ CH N CH N t-Bu Cl CF₃ CF₃ CH N CH N Et Cl CF₃ OMe CH N CH N i-Pr Cl CF₃ OMe CH N CH N t-Bu Cl CF₃ OMe CH N CH N Et Cl CF₃ CN CH N CH N i-Pr Cl CF₃ CN CH N CH N t-Bu Cl CF₃ CN CH CH CH CCl Et Me CF₃ Cl CH CH CH CCl i-Pr Me CF₃ Cl CH CH CH CCl t-Bu Me CF₃ Cl CH CH CH CCl Et Me CF₃ Br CH CH CH CCl i-Pr Me CF₃ Br CH CH CH CCl t-Bu Me CF₃ Br CH CH CH CCl Et Me CF₃ I CH CH CH CCl i-Pr Me CF₃ I CH CH CH CCl t-Bu Me CF₃ I CH CH CH CCl Et Me CF₃ F CH CH CH CCl i-Pr Me CF₃ F CH CH CH CCl t-Bu Me CF₃ F CH CH CH CCl Et Me CF₃ Me CH CH CH CCl i-Pr Me CF₃ Me CH CH CH CCl t-Bu Me CF₃ Me CH CH CH CCl Et Me CF₃ CF₃ CH CH CH CCl i-Pr Me CF₃ CF₃ CH CH CH CCl t-Bu Me CF₃ CF₃ CH CH CH CCl Et Me CF₃ OMe CH CH CH CCl i-Pr Me CF₃ OMe CH CH CH CCl t-Bu Me CF₃ OMe CH CH CH CCl Et Me CF₃ CN CH CH CH CCl i-Pr Me CF₃ CN CH CH CH CCl t-Bu Me CF₃ CN CH CH CH CCl Et Cl CF₃ Cl CH CH CH CCl i-Pr Cl CF₃ Cl CH CH CH CCl t-Bu Cl CF₃ Cl CH CH CH CCl Et Cl CF₃ Br CH CH CH CCl i-Pr Cl CF₃ Br CH CH CH CCl t-Bu Cl CF₃ Br CH CH CH CCl Et Cl CF₃ I CH CH CH CCl i-Pr Cl CF₃ I CH CH CH CCl t-Bu Cl CF₃ I CH CH CH CCl Et Cl CF₃ F CH CH CH CCl i-Pr Cl CF₃ F CH CH CH CCl t-Bu Cl CF₃ F CH CH CH CCl Et Cl CF₃ Me CH CH CH CCl i-Pr Cl CF₃ Me CH CH CH CCl t-Bu Cl CF₃ Me CH CH CH CCl Et Cl CF₃ CF₃ CH CH CH CCl i-Pr Cl CF₃ CF₃ CH CH CH CCl t-Bu Cl CF₃ CF₃ CH CH CH CCl Et Cl CF₃ OMe CH CH CH CCl i-Pr Cl CF₃ OMe CH CH CH CCl t-Bu Cl CF₃ OMe CH CH CH CCl Et Cl CF₃ CN CH CH CH CCl i-Pr Cl CF₃ CN CH CH CH CCl t-Bu Cl CF₃ CN CH CH CH CF Et Me CF₃ Cl CH CH CH CF i-Pr Me CF₃ Cl CH CH CH CF t-Bu Me CF₃ Cl CH CH CH CF Et Me CF₃ Br CH CH CH CF i-Pr Me CF₃ Br CH CH CH CF t-Bu Me CF₃ Br CH CH CH CF Et Me CF₃ I CH CH CH CF i-Pr Me CF₃ I CH CH CH CF t-Bu Me CF₃ I CH CH CH CF Et Me CF₃ F CH CH CH CF i-Pr Me CF₃ F CH CH CH CF t-Bu Me CF₃ F CH CH CH CF Et Me CF₃ Me CH CH CH CF i-Pr Me CF₃ Me CH CH CH CF t-Bu Me CF₃ Me CH CH CH CF Et Me CF₃ CF₃ CH CH CH CF i-Pr Me CF₃ CF₃ CH CH CH CF t-Bu Me CF₃ CF₃ CH CH CH CF Et Me CF₃ OMe CH CH CH CF i-Pr Me CF₃ OMe CH CH CH CF t-Bu Me CF₃ OMe CH CH CH CF Et Me CF₃ CN CH CH CH CF i-Pr Me CF₃ CN CH CH CH CF t-Bu Me CF₃ CN CH CH CH CF Et Cl CF₃ Cl CH CH CH CF i-Pr Cl CF₃ Cl CH CH CH CF t-Bu Cl CF₃ Cl CH CH CH CF Et Cl CF₃ Br CH CH CH CF i-Pr Cl CF₃ Br CH CH CH CF t-Bu Cl CF₃ Br CH CH CH CF Et Cl CF₃ I CH CH CH CF i-Pr Cl CF₃ I CH CH CH CF t-Bu Cl CF₃ I CH CH CH CF i-Pr Cl CF₃ F CH CH CH CF t-Bu Cl CF₃ F CH CH CH CF Et Cl CF₃ Me CH CH CH CF i-Pr Cl CF₃ Me CH CH CH CF t-Bu Cl CF₃ Me CH CH CH CF Et Cl CF₃ CF₃ CH CH CH CF i-Pr Cl CF₃ CF₃ CH CH CH CF t-Bu Cl CF₃ CF₃ CH CH CH CF Et Cl CF₃ OMe CH CH CH CF i-Pr Cl CF₃ OMe CH CH CH CF t-Bu Cl CF₃ OMe CH CH CH CF Et Cl CF₃ CN CH CH CH CF i-Pr Cl CF₃ CN CH CH CH CF t-Bu Cl CF₃ CN CH CH CH CH Et Me C₂F₅ Cl CH CH CH CH i-Pr Me C₂F₅ Cl CH CH CH CH t-Bu Me C₂F₅ Cl CH CH CH CH Et Me C₂F₅ Br CH CH CH CH i-Pr Me C₂F₅ Br CH CH CH CH t-Bu Me C₂F₅ Br CH CH CH CH Et Me C₂F₅ I CH CH CH CH i-Pr Me C₂F₅ I CH CH CH CH t-Bu Me C₂F₅ I CH CH CH CH Et Me C₂F₅ F CH CH CH CH i-Pr Me C₂F₅ F CH CH CH CH t-Bu Me C₂F₅ F CH CH CH CH Et Me C₂F₅ Me CH CH CH CH i-Pr Me C₂F₅ Me CH CH CH CH t-Bu Me C₂F₅ Me CH CH CH CH Et Me C₂F₅ CF₃ CH CH CH CH i-Pr Me C₂F₅ CF₃ CH CH CH CH t-Bu Me C₂F₅ CF₃ CH CH CH CH Et Me C₂F₅ OMe CH CH CH CH i-Pr Me C₂F₅ OMe CH CH CH CH t-Bu Me C₂F₅ OMe CH CH CH CH Et Me C₂F₅ CN CH CH CH CH i-Pr Me C₂F₅ CN CH CH CH CH t-Bu Me C₂F₅ CN CH CH CH CH Et Cl C₂F₅ Cl CH CH CH CH i-Pr Cl C₂F₅ Cl CH CH CH CH t-Bu Cl C₂F₅ Cl CH CH CH CH Et Cl C₂F₅ Br CH CH CH CH i-Pr Cl C₂F₅ Br CH CH CH CH t-Bu Cl C₂F₅ Br CH CH CH CH Et Cl C₂F₅ I CH CH CH CH i-Pr Cl C₂F₅ I CH CH CH CH t-Bu Cl C₂F₅ I CH CH CH CH Et Cl C₂F₅ F CH CH CH CH i-Pr Cl C₂F₅ F CH CH CH CH t-Bu Cl C₂F₅ F CH CH CH CH Et Cl C₂F₅ Me CH CH CH CH i-Pr Cl C₂F₅ Me CH CH CH CH t-Bu Cl C₂F₅ Me CH CH CH CH Et Cl C₂F₅ CF₃ CH CH CH CH i-Pr Cl C₂F₅ CF₃ CH CH CH CH t-Bu Cl C₂F₅ CF₃ CH CH CH CH Et Cl C₂F₅ OMe CH CH CH CH i-Pr Cl C₂F₅ OMe CH CH CH CH t-Bu Cl C₂F₅ OMe CH CH CH CH Et Cl C₂F₅ CN CH CH CH CH i-Pr Cl C₂F₅ CN CH CH CH CH t-Bu Cl C₂F₅ CN

TABLE 13

W X Y Z R³ R⁴ R⁷ R⁸ CH CH CH CH Et Me CF₃ Cl CH CH CH CH i-Pr Me CF₃ Cl CH CH CH CH t-Bu Me CF₃ Cl CH CH CH CH Et Me CF₃ Br CH CH CH CH i-Pr Me CF₃ Br CH CH CH CH t-Bu Me CF₃ Br CH CH CH CH Et Me CF₃ I CH CH CH CH i-Pr Me CF₃ I CH CH CH CH t-Bu Me CF₃ I CH CH CH CH Et Me CF₃ F CH CH CH CH i-Pr Me CF₃ F CH CH CH CH t-Bu Me CF₃ F CH CH CH CH Et Me CF₃ Me CH CH CH CH i-Pr Me CF₃ Me CH CH CH CH t-Bu Me CF₃ Me CH CH CH CH Et Me CF₃ CF₃ CH CH CH CH i-Pr Me CF₃ CF₃ CH CH CH CH t-Bu Me CF₃ CF₃ CH CH CH CH Et Me CF₃ OMe CH CH CH CH i-Pr Me CF₃ OMe CH CH CH CH t-Bu Me CF₃ OMe CH CH CH CH Et Me CF₃ CN CH CH CH CH i-Pr Me CF₃ CN CH CH CH CH t-Bu Me CF₃ CN CH CH CH CH Et Cl CF₃ Cl CH CH CH CH i-Pr Cl CF₃ Cl CH CH CH CH t-Bu Cl CF₃ Cl CH CH CH CH Et Cl CF₃ Br CH CH CH CH i-Pr Cl CF₃ Br CH CH CH CH t-Bu Cl CF₃ Br CH CH CH CH Et Cl CF₃ I CH CH CH CH i-Pr Cl CF₃ I CH CH CH CH t-Bu Cl CF₃ I CH CH CH CH Et Cl CF₃ F CH CH CH CH i-Pr Cl CF₃ F CH CH CH CH t-Bu Cl CF₃ F CH CH CH CH Et Cl CF₃ Me CH CH CH CH i-Pr Cl CF₃ Me CH CH CH CH t-Bu Cl CF₃ Me CH CH CH CH Et Cl CF₃ CF₃ CH CH CH CH i-Pr Cl CF₃ CF₃ CH CH CH CH t-Bu Cl CF₃ CF₃ CH CH CH CH Et Cl CF₃ OMe CH CH CH CH i-Pr Cl CF₃ OMe CH CH CH CH t-Bu Cl CF₃ OMe CH CH CH CH Et Cl CF₃ CN CH CH CH CH i-Pr Cl CF₃ CN CH CH CH CH t-Bu Cl CF₃ CN CH CH CH N Et Me CF₃ Cl CH CH CH N i-Pr Me CF₃ Cl CH CH CH N t-Bu Me CF₃ Cl CH CH CH N Et Me CF₃ Br CH CH CH N i-Pr Me CF₃ Br CH CH CH N t-Bu Me CF₃ Br CH CH CH N Et Me CF₃ I CH CH CH N i-Pr Me CF₃ I CH CH CH N t-Bu Me CF₃ I CH CH CH N Et Me CF₃ F CH CH CH N i-Pr Me CF₃ F CH CH CH N t-Bu Me CF₃ F CH CH CH N Et Me CF₃ Me CH CH CH N i-Pr Me CF₃ Me CH CH CH N t-Bu Me CF₃ Me CH CH CH N Et Me CF₃ CF₃ CH CH CH N i-Pr Me CF₃ CF₃ CH CH CH N t-Bu Me CF₃ CF₃ CH CH CH N Et Me CF₃ OMe CH CH CH N i-Pr Me CF₃ OMe CH CH CH N t-Bu Me CF₃ OMe CH CH CH N Et Me CF₃ CN CH CH CH N i-Pr Me CF₃ CN CH CH CH N t-Bu Me CF₃ CN CH CH CH N Et Cl CF₃ Cl CH CH CH N i-Pr Cl CF₃ Cl CH CH CH N t-Bu Cl CF₃ Cl CH CH CH N Et Cl CF₃ Br CH CH CH N i-Pr Cl CF₃ Br CH CH CH N t-Bu Cl CF₃ Br CH CH CH N Et Cl CF₃ I CH CH CH N i-Pr Cl CF₃ I CH CH CH N t-Bu Cl CF₃ I CH CH CH N Et Cl CF₃ F CH CH CH N i-Pr Cl CF₃ F CH CH CH N t-Bu Cl CF₃ F CH CH CH N Et Cl CF₃ Me CH CH CH N i-Pr Cl CF₃ Me CH CH CH N t-Bu Cl CF₃ Me CH CH CH N Et Cl CF₃ CF₃ CH CH CH N i-Pr Cl CF₃ CF₃ CH CH CH N t-Bu Cl CF₃ CF₃ CH CH CH N Et Cl CF₃ OMe CH CH CH N i-Pr Cl CF₃ OMe CH CH CH N t-Bu Cl CF₃ OMe CH CH CH N Et Cl CF₃ CN CH CH CH N i-Pr Cl CF₃ CN CH CH CH N t-Bu Cl CF₃ CN CH CH N CH Et Me CF₃ Cl CH CH N CH i-Pr Me CF₃ Cl CH CH N CH t-Bu Me CF₃ Cl CH CH N CH Et Me CF₃ Br CH CH N CH i-Pr Me CF₃ Br CH CH N CH t-Bu Me CF₃ Br CH CH N CH Et Me CF₃ I CH CH N CH i-Pr Me CF₃ I CH CH N CH t-Bu Me CF₃ I CH CH N CH Et Me CF₃ F CH CH N CH i-Pr Me CF₃ F CH CH N CH t-Bu Me CF₃ F CH CH N CH Et Me CF₃ Me CH CH N CH i-Pr Me CF₃ Me CH CH N CH t-Bu Me CF₃ Me CH CH N CH Et Me CF₃ CF₃ CH CH N CH i-Pr Me CF₃ CF₃ CH CH N CH t-Bu Me CF₃ CF₃ CH CH N CH Et Me CF₃ OMe CH CH N CH i-Pr Me CF₃ OMe CH CH N CH t-Bu Me CF₃ OMe CH CH N CH Et Me CF₃ CN CH CH N CH i-Pr Me CF₃ CN CH CH N CH t-Bu Me CF₃ CN CH CH N CH Et Cl CF₃ Cl CH CH N CH i-Pr Cl CF₃ Cl CH CH N CH t-Bu Cl CF₃ Cl CH CH N CH Et Cl CF₃ Br CH CH N CH i-Pr Cl CF₃ Br CH CH N CH t-Bu Cl CF₃ Br CH CH N CH Et Cl CF₃ I CH CH N CH i-Pr Cl CF₃ I CH CH N CH t-Bu Cl CF₃ I CH CH N CH Et Cl CF₃ F CH CH N CH i-Pr Cl CF₃ F CH CH N CH t-Bu Cl CF₃ F CH CH N CH Et Cl CF₃ Me CH CH N CH i-Pr Cl CF₃ Me CH CH N CH t-Bu Cl CF₃ Me CH CH N CH Et Cl CF₃ CF₃ CH CH N CH i-Pr Cl CF₃ CF₃ CH CH N CH t-Bu Cl CF₃ CF₃ CH CH N CH Et Cl CF₃ OMe CH CH N CH i-Pr Cl CF₃ OMe CH CH N CH t-Bu Cl CF₃ OMe CH CH N CH Et Cl CF₃ CN CH CH N CH i-Pr Cl CF₃ CN CH CH N CH t-Bu Cl CF₃ CN CH N CH CH Et Me CF₃ Cl CH N CH CH i-Pr Me CF₃ Cl CH N CH CH t-Bu Me CF₃ Cl CH N CH CH Et Me CF₃ Br CH N CH CH i-Pr Me CF₃ Br CH N CH CH t-Bu Me CF₃ Br CH N CH CH Et Me CF₃ I CH N CH CH i-Pr Me CF₃ I CH N CH CH t-Bu Me CF₃ I CH N CH CH Et Me CF₃ F CH N CH CH i-Pr Me CF₃ F CH N CH CH t-Bu Me CF₃ F CH N CH CH Et Me CF₃ Me CH N CH CH i-Pr Me CF₃ Me CH N CH CH t-Bu Me CF₃ Me CH N CH CH Et Me CF₃ CF₃ CH N CH CH i-Pr Me CF₃ CF₃ CH N CH CH t-Bu Me CF₃ CF₃ CH N CH CH Et Me CF₃ OMe CH N CH CH i-Pr Me CF₃ OMe CH N CH CH t-Bu Me CF₃ OMe CH N CH CH Et Me CF₃ CN CH N CH CH i-Pr Me CF₃ CN CH N CH CH t-Bu Me CF₃ CN CH N CH CH Et Cl CF₃ Cl CH N CH CH i-Pr Cl CF₃ Cl CH N CH CH t-Bu Cl CF₃ Cl CH N CH CH Et Cl CF₃ Br CH N CH CH i-Pr Cl CF₃ Br CH N CH CH t-Bu Cl CF₃ Br CH N CH CH Et Cl CF₃ I CH N CH CH i-Pr Cl CF₃ I CH N CH CH t-Bu Cl CF₃ I CH N CH CH Et Cl CF₃ F CH N CH CH i-Pr Cl CF₃ F CH N CH CH t-Bu Cl CF₃ F CH N CH CH Et Cl CF₃ Me CH N CH CH i-Pr Cl CF₃ Me CH N CH CH t-Bu Cl CF₃ Me CH N CH CH Et Cl CF₃ CF₃ CH N CH CH i-Pr Cl CF₃ CF₃ CH N CH CH t-Bu Cl CF₃ CF₃ CH N CH CH Et Cl CF₃ OMe CH N CH CH i-Pr Cl CF₃ OMe CH N CH CH t-Bu Cl CF₃ OMe CH N CH CH Et Cl CF₃ CN CH N CH CH i-Pr Cl CF₃ CN CH N CH CH t-Bu Cl CF₃ CN N CH CH CH Et Me CF₃ Cl N CH CH CH i-Pr Me CF₃ Cl N CH CH CH t-Bu Me CF₃ Cl N CH CH CH Et Me CF₃ Br N CH CH CH i-Pr Me CF₃ Br N CH CH CH t-Bu Me CF₃ Br N CH CH CH Et Me CF₃ I N CH CH CH i-Pr Me CF₃ I N CH CH CH t-Bu Me CF₃ I N CH CH CH Et Me CF₃ F N CH CH CH i-Pr Me CF₃ F N CH CH CH t-Bu Me CF₃ F N CH CH CH Et Me CF₃ Me N CH CH CH i-Pr Me CF₃ Me N CH CH CH t-Bu Me CF₃ Me N CH CH CH Et Me CF₃ CF₃ N CH CH CH i-Pr Me CF₃ CF₃ N CH CH CH t-Bu Me CF₃ CF₃ N CH CH CH Et Me CF₃ OMe N CH CH CH i-Pr Me CF₃ OMe N CH CH CH t-Bu Me CF₃ OMe N CH CH CH Et Me CF₃ CN N CH CH CH i-Pr Me CF₃ CN N CH CH CH t-Bu Me CF₃ CN N CH CH CH Et Cl CF₃ Cl N CH CH CH i-Pr Cl CF₃ Cl N CH CH CH t-Bu Cl CF₃ Cl N CH CH CH Et Cl CF₃ Br N CH CH CH i-Pr Cl CF₃ Br N CH CH CH t-Bu Cl CF₃ Br N CH CH CH Et Cl CF₃ I N CH CH CH i-Pr Cl CF₃ I N CH CH CH t-Bu Cl CF₃ I N CH CH CH Et Cl CF₃ F N CH CH CH i-Pr Cl CF₃ F N CH CH CH t-Bu Cl CF₃ F N CH CH CH Et Cl CF₃ Me N CH CH CH i-Pr Cl CF₃ Me N CH CH CH t-Bu Cl CF₃ Me N CH CH CH Et Cl CF₃ CF₃ N CH CH CH i-Pr Cl CF₃ CF₃ N CH CH CH t-Bu Cl CF₃ CF₃ N CH CH CH Et Cl CF₃ OMe N CH CH CH i-Pr Cl CF₃ OMe N CH CH CH t-Bu Cl CF₃ OMe N CH CH CH Et Cl CF₃ CN N CH CH CH i-Pr Cl CF₃ CN N CH CH CH t-Bu Cl CF₃ CN CH N CH N Et Me CF₃ Cl CH N CH N i-Pr Me CF₃ Cl CH N CH N t-Bu Me CF₃ Cl CH N CH N Et Me CF₃ Br CH N CH N i-Pr Me CF₃ Br CH N CH N t-Bu Me CF₃ Br CH N CH N Et Me CF₃ I CH N CH N i-Fr Me CF₃ I CH N CH N t-Bu Me CF₃ I CH N CH N Et Me CF₃ F CH N CH N i-Pr Me CF₃ F CH N CH N t-Bu Me CF₃ F CH N CH N Et Me CF₃ Me CH N CH N i-Pr Me CF₃ Me CH N CH N t-Bu Me CF₃ Me CH N CH N Et Me CF₃ CF₃ CH N CH N i-Pr Me CF₃ CF₃ CH N CH N t-Bu Me CF₃ CF₃ CH N CH N Et Me CF₃ OMe CH N CH N i-Pr Me CF₃ OMe CH N CH N t-Bu Me CF₃ OMe CH N CH N Et Me CF₃ CN CH N CH N i-Pr Me CF₃ CN CH N CH N t-Bu Me CF₃ CN CH N CH N Et Cl CF₃ Cl CH N CH N i-Pr Cl CF₃ Cl CH N CH N t-Bu Cl CF₃ Cl CH N CH N Et Cl CF₃ Br CH N CH N i-Pr Cl CF₃ Br CH N CH N t-Bu Cl CF₃ Br CH N CH N Et Cl CF₃ I CH N CH N i-Pr Cl CF₃ I CH N CH N t-Bu Cl CF₃ I CH N CH N Et Cl CF₃ F CH N CH N i-Pr Cl CF₃ F CH N CH N t-Bu Cl CF₃ F CH N CH N Et Cl CF₃ Me CH N CH N i-Pr Cl CF₃ Me CH N CH N t-Bu Cl CF₃ Me CH N CH N Et Cl CF₃ CF₃ CH N CH N i-Pr Cl CF₃ CF₃ CH N CH N t-Bu Cl CF₃ CF₃ CH N CH N Et Cl CF₃ OMe CH N CH N i-Pr Cl CF₃ OMe CH N CH N t-Bu Cl CF₃ OMe CH N CH N Et Cl CF₃ CN CH N CH N i-Pr Cl CF₃ CN CH N CH N t-Bu Cl CF₃ CN CH CH CH CCl Et Me CF₃ Cl CH CH CH CCl i-Pr Me CF₃ Cl CH CH CH CCl t-Bu Me CF₃ Cl CH CH CH CCl Et Me CF₃ Br CH CH CH CCl i-Pr Me CF₃ Br CH CH CH CCl t-Bu Me CF₃ Br CH CH CH CCl Et Me CF₃ I CH CH CH CCl i-Pr Me CF₃ I CH CH CH CCl t-Bu Me CF₃ I CH CH CH CCl Et Me CF₃ F CH CH CH CCl i-Pr Me CF₃ F CH CH CH CCl t-Bu Me CF₃ F CH CH CH CCl Et Me CF₃ Me CH CH CH CCl i-Pr Me CF₃ Me CH CH CH CCl t-Bu Me CF₃ Me CH CH CH CCl Et Me CF₃ CF₃ CH CH CH CCl i-Pr Me CF₃ CF₃ CH CH CH CCl t-Bu Me CF₃ CF₃ CH CH CH CCl Et Me CF₃ OMe CH CH CH CCl i-Pr Me CF₃ OMe CH CH CH CCl t-Bu Me CF₃ OMe CH CH CH CCl Et Me CF₃ CN CH CH CH CCl i-Pr Me CF₃ CN CH CH CH CCl t-Bu Me CF₃ CN CH CH CH CCl Et Cl CF₃ Cl CH CH CH CCl i-Pr Cl CF₃ Cl CH CH CH CCl t-Bu Cl CF₃ Cl CH CH CH CCl Et Cl CF₃ Br CH CH CH CCl i-Pr Cl CF₃ Br CH CH CH CCl t-Bu Cl CF₃ Br CH CH CH CCl Et Cl CF₃ I CH CH CH CCl i-Pr Cl CF₃ I CH CH CH CCl t-Bu Cl CF₃ I CH CH CH CCl Et Cl CF₃ F CH CH CH CCl i-Pr C CF₃ F CH CH CH CCl t-Bu Cl CF₃ F CH CH CH CCl Et Cl CF₃ Me CH CH CH CCl i-Pr Cl CF₃ Me CH CH CH CCl t-Bu Cl CF₃ Me CH CH CH CCl Et Cl CF₃ CF₃ CH CH CH CCl i-Pr Cl CF₃ CF₃ CH CH CH CCl t-Bu Cl CF₃ CF₃ CH CH CH CCl Et Cl CF₃ OMe CH CH CH CCl i-Pr Cl CF₃ OMe CH CH CH CCl t-Bu Cl CF₃ OMe CH CH CH CCl Et Cl CF₃ CN CH CH CH CCl i-Pr Cl CF₃ CN CH CH CH CCl t-Bu Cl CF₃ CN CH CH CH CF Et Me CF₃ Cl CH CH CH CF i-Pr Me CF₃ Cl CH CH CH CF t-Bu Me CF₃ Cl CH CH CH CF Et Me CF₃ Br CH CH CH CF i-Pr Me CF₃ Br CH CH CH CF t-Bu Me CF₃ Br CH CH CH CF Et Me CF₃ I CH CH CH CF i-Pr Me CF₃ I CH CH CH CF t-Bu Me CF₃ I CH CH CH CF Et Me CF₃ F CH CH CH CF i-Pr Me CF₃ F CH CH CH CF t-Bu Me CF₃ F CH CH CH CF Et Me CF₃ Me CH CH CH CF i-Pr Me CF₃ Me CH CH CH CF t-Bu Me CF₃ Me CH CH CH CF Et Me CF₃ CF₃ CH CH CH CF i-Pr Me CF₃ CF₃ CH CH CH CF t-Bu Me CF₃ CF₃ CH CH CH CF Et Me CF₃ OMe CH CH CH CF i-Pr Me CF₃ OMe CH CH CH CF t-Bu Me CF₃ OMe CH CH CH CF Et Me CF₃ CN CH CH CH CF i-Pr Me CF₃ CN CH CH CH CF t-Bu Me CF₃ CN CH CH CH CF Et Cl CF₃ Cl CH CH CH CF i-Pr Cl CF₃ Cl CH CH CH CF t-Bu Cl CF₃ Cl CH CH CH CF Et Cl CF₃ Br CH CH CH CF i-Pr Cl CF₃ Br CH CH CH CF t-Bu Cl CF₃ Br CH CH CH CF Et Cl CF₃ I CH CH CH CF i-Pr Cl CF₃ I CH CH CH CF t-Bu Cl CF₃ I CH CH CH CF i-Pr Cl CF₃ F CH CH CH CF t-Bu Cl CF₃ F CH CH CH CF Et Cl CF₃ Me CH CH CH CF i-Pr Cl CF₃ Me CH CH CH CF t-Bu Cl CF₃ Me CH CH CH CF Et Cl CF₃ CF₃ CH CH CH CF i-Pr Cl CF₃ CF₃ CH CH CH CF t-Bu Cl CF₃ CF₃ CH CH CH CF Et Cl CF₃ OMe CH CH CH CF i-Pr Cl CF₃ OMe CH CH CH CF t-Bu Cl CF₃ OMe CH CH CH CF Et Cl CF₃ CN CH CH CH CF i-Pr Cl CF₃ CN CH CH CH CF t-Bu Cl CF₃ CN CH CH CH CH Et Me C₂F₅ Cl CH CH CH CH i-Pr Me C₂F₅ Cl CH CH CH CH t-Bu Me C₂F₅ Cl CH CH CH CH Et Me C₂F₅ Br CH CH CH CH i-Pr Me C₂F₅ Br CH CH CH CH t-Bu Me C₂F₅ Br CH CH CH CH Et Me C₂F₅ I CH CH CH CH i-Pr Me C₂F₅ I CH CH CH CH t-Bu Me C₂F₅ I CH CH CH CH Et Me C₂F₅ F CH CH CH CH i-Pr Me C₂F₅ F CH CH CH CH t-Bu Me C₂F₅ F CH CH CH CH Et Me C₂F₅ Me CH CH CH CH i-Pr Me C₂F₅ Me CH CH CH CH t-Bu Me C₂F₅ Me CH CH CH CH Et Me C₂F₅ CF₃ CH CH CH CH i-Pr Me C₂F₅ CF₃ CH CH CH CH t-Bu Me C₂F₅ CF₃ CH CH CH CH Et Me C₂F₅ OMe CH CH CH CH i-Pr Me C₂F₅ OMe CH CH CH CH t-Bu Me C₂F₅ OMe CH CH CH CH Et Me C₂F₅ CN CH CH CH CH i-Pr Me C₂F₅ CN CH CH CH CH t-Bu Me C₂F₅ CN CH CH CH CH Et Cl C₂F₅ Cl CH CH CH CH i-Pr Cl C₂F₅ Cl CH CH CH CH t-Bu Cl C₂F₅ Cl CH CH CH CH Et Cl C₂F₅ Br CH CH CH CH i-Pr Cl C₂F₅ Br CH CH CH CH t-Bu Cl C₂F₅ Br CH CH CH CH Et Cl C₂F₅ I CH CH CH CH i-Pr Cl C₂F₅ I CH CH CH CH t-Bu Cl C₂F₅ I CH CH CH CH Et Cl C₂F₅ F CH CH CH CH i-Pr Cl C₂F₅ F CH CH CH CH t-Bu Cl C₂F₅ F CH CH CH CH Et Cl C₂F₅ Me CH CH CH CH i-Pr Cl C₂F₅ Me CH CH CH CH t-Bu Cl C₂F₅ Me CH CH CH CH Et Cl C₂F₅ CF₃ CH CH CH CH i-Pr Cl C₂F₅ CF₃ CH CH CH CH t-Bu Cl C₂F₅ CF₃ CH CH CH CH Et Cl C₂F₅ OMe CH CH CH CH i-Pr Cl C₂F₅ OMe CH CH CH CH t-Bu Cl C₂F₅ OMe CH CH CH CH Et Cl C₂F₅ CN CH CH CH CH i-Pr Cl C₂F₅ CN CH CH CH CH t-Bu Cl C₂F₅ CN

TABLE 14

W X Y Z R³ R⁴ R⁷ R⁸ CH CH CH CH Et Me CF₃ Cl CH CH CH CH i-Pr Me CF₃ Cl CH CH CH CH t-Bu Me CF₃ Cl CH CH CH CH Et Me CF₃ Br CH CH CH CH i-Pr Me CF₃ Br CH CH CH CH t-Bu Me CF₃ Br CH CH CH CH Et Me CF₃ I CH CH CH CH i-Pr Me CF₃ I CH CH CH CH t-Bu Me CF₃ I CH CH CH CH Et Me CF₃ F CH CH CH CH i-Pr Me CF₃ F CH CH CH CH t-Bu Me CF₃ F CH CH CH CH Et Me CF₃ Me CH CH CH CH i-Pr Me CF₃ Me CH CH CH CH t-Bu Me CF₃ Me CH CH CH CH Et Me CF₃ CF₃ CH CH CH CH i-Pr Me CF₃ CF₃ CH CH CH CH t-Bu Me CF₃ CF₃ CH CH CH CH Et Me CF₃ OMe CH CH CH CH i-Pr Me CF₃ OMe CH CH CH CH t-Bu Me CF₃ OMe CH CH CH CH Et Me CF₃ CN CH CH CH CH i-Pr Me CF₃ CN CH CH CH CH t-Bu Me CF₃ CN CH CH CH CH Et Cl CF₃ Cl CH CH CH CH i-Pr Cl CF₃ Cl CH CH CH CH t-Bu Cl CF₃ Cl CH CH CH CH Et Cl CF₃ Br CH CH CH CH i-Pr Cl CF₃ Br CH CH CH CH t-Bu Cl CF₃ Br CH CH CH CH Et Cl CF₃ I CH CH CH CH i-Pr Cl CF₃ I CH CH CH CH t-Bu Cl CF₃ I CH CH CH CH Et Cl CF₃ F CH CH CH CH i-Pr Cl CF₃ F CH CH CH CH t-Bu Cl CF₃ F CH CH CH CH Et Cl CF₃ Me CH CH CH CH i-Pr Cl CF₃ Me CH CH CH CH t-Bu Cl CF₃ Me CH CH CH CH Et Cl CF₃ CF₃ CH CH CH CH i-Pr Cl CF₃ CF₃ CH CH CH CH t-Bu Cl CF₃ CF₃ CH CH CH CH Et Cl CF₃ OMe CH CH CH CH i-Pr Cl CF₃ OMe CH CH CH CH t-Bu Cl CF₃ OMe CH CH CH CH Et Cl CF₃ CN CH CH CH CH i-Pr Cl CF₃ CN CH CH CH CH t-Bu Cl CF₃ CN CH CH CH N Et Me CF₃ Cl CH CH CH N i-Pr Me CF₃ Cl CH CH CH N t-Bu Me CF₃ Cl CH CH CH N Et Me CF₃ Br CH CH CH N i-Pr Me CF₃ Br CH CH CH N t-Bu Me CF₃ Br CH CH CH N Et Me CF₃ I CH CH CH N i-Pr Me CF₃ I CH CH CH N t-Bu Me CF₃ I CH CH CH N Et Me CF₃ F CH CH CH N i-Pr Me CF₃ F CH CH CH N t-Bu Me CF₃ F CH CH CH N Et Me CF₃ Me CH CH CH N i-Pr Me CF₃ Me CH CH CH N t-Bu Me CF₃ Me CH CH CH N Et Me CF₃ CF₃ CH CH CH N i-Pr Me CF₃ CF₃ CH CH CH N t-Bu Me CF₃ CF₃ CH CH CH N Et Me CF₃ OMe CH CH CH N i-Pr Me CF₃ OMe CH CH CH N t-Bu Me CF₃ OMe CH CH CH N Et Me CF₃ CN CH CH CH N i-Pr Me CF₃ CN CH CH CH N t-Bu Me CF₃ CN CH CH CH N Et Cl CF₃ Cl CH CH CH N i-Pr Cl CF₃ Cl CH CH CH N t-Bu Cl CF₃ Cl CH CH CH N Et Cl CF₃ Br CH CH CH N i-Pr Cl CF₃ Br CH CH CH N t-Bu Cl CF₃ Br CH CH CH N Et Cl CF₃ I CH CH CH N i-Pr Cl CF₃ I CH CH CH N t-Bu Cl CF₃ I CH CH CH N Et Cl CF₃ F CH CH CH N i-Pr Cl CF₃ F CH CH CH N t-Bu Cl CF₃ F CH CH CH N Et Cl CF₃ Me CH CH CH N i-Pr Cl CF₃ Me CH CH CH N t-Bu Cl CF₃ Me CH CH CH N Et Cl CF₃ CF₃ CH CH CH N i-Pr Cl CF₃ CF₃ CH CH CH N t-Bu Cl CF₃ CF₃ CH CH CH N Et Cl CF₃ OMe CH CH CH N i-Pr Cl CF₃ OMe CH CH CH N t-Bu Cl CF₃ OMe CH CH CH N Et Cl CF₃ CN CH CH CH N i-Pr Cl CF₃ CN CH CH CH N t-Bu Cl CF₃ CN CH CH N CH Et Me CF₃ Cl CH CH N CH i-Pr Me CF₃ Cl CH CH N CH t-Bu Me CF₃ Cl CH CH N CH Et Me CF₃ Br CH CH N CH i-Pr Me CF₃ Br CH CH N CH t-Bu Me CF₃ Br CH CH N CH Et Me CF₃ I CH CH N CH i-Pr Me CF₃ I CH CH N CH t-Bu Me CF₃ I CH CH N CH Et Me CF₃ F CH CH N CH i-Pr Me CF₃ F CH CH N CH t-Bu Me CF₃ F CH CH N CH Et Me CF₃ Me CH CH N CH i-Pr Me CF₃ Me CH CH N CH t-Bu Me CF₃ Me CH CH N CH Et Me CF₃ CF₃ CH CH N CH i-Pr Me CF₃ CF₃ CH CH N CH t-Bu Me CF₃ CF₃ CH CH N CH Et Me CF₃ OMe CH CH N CH i-Pr Me CF₃ OMe CH CH N CH t-Bu Me CF₃ OMe CH CH N CH Et Me CF₃ CN CH CH N CH i-Pr Me CF₃ CN CH CH N CH t-Bu Me CF₃ CN CH CH N CH Et Cl CF₃ Cl CH CH N CH i-Pr Cl CF₃ Cl CH CH N CH t-Bu Cl CF₃ Cl CH CH N CH Et Cl CF₃ Br CH CH N CH i-Pr Cl CF₃ Br CH CH N CH t-Bu Cl CF₃ Br CH CH N CH Et Cl CF₃ I CH CH N CH i-Pr Cl CF₃ I CH CH N CH t-Bu Cl CF₃ I CH CH N CH Et Cl CF₃ F CH CH N CH i-Pr Cl CF₃ F CH CH N CH t-Bu Cl CF₃ F CH CH N CH Et Cl CF₃ Me CH CH N CH i-Pr Cl CF₃ Me CH CH N CH t-Bu Cl CF₃ Me CH CH N CH Et Cl CF₃ CF₃ CH CH N CH i-Pr Cl CF₃ CF₃ CH CH N CH t-Bu Cl CF₃ CF₃ CH CH N CH Et Cl CF₃ OMe CH CH N CH i-Pr Cl CF₃ OMe CH CH N CH t-Bu Cl CF₃ OMe CH CH N CH Et Cl CF₃ CN CH CH N CH i-Pr Cl CF₃ CN CH CH N CH t-Bu Cl CF₃ CN CH N CH CH Et Me CF₃ Cl CH N CH CH i-Pr Me CF₃ Cl CH N CH CH t-Bu Me CF₃ Cl CH N CH CH Et Me CF₃ Br CH N CH CH i-Pr Me CF₃ Br CH N CH CH t-Bu Me CF₃ Br CH N CH CH Et Me CF₃ I CH N CH CH i-Pr Me CF₃ I CH N CH CH t-Bu Me CF₃ I CH N CH CH Et Me CF₃ F CH N CH CH i-Pr Me CF₃ F CH N CH CH t-Bu Me CF₃ F CH N CH CH Et Me CF₃ Me CH N CH CH i-Pr Me CF₃ Me CH N CH CH t-Bu Me CF₃ Me CH N CH CH Et Me CF₃ CF₃ CH N CH CH i-Pr Me CF₃ CF₃ CH N CH CH t-Bu Me CF₃ CF₃ CH N CH CH Et Me CF₃ OMe CH N CH CH i-Pr Me CF₃ OMe CH N CH CH t-Bu Me CF₃ OMe CH N CH CH Et Me CF₃ CN CH N CH CH i-Pr Me CF₃ CN CH N CH CH t-Bu Me CF₃ CN CH N CH CH Et Cl CF₃ Cl CH N CH CH i-Pr Cl CF₃ Cl CH N CH CH t-Bu Cl CF₃ Cl CH N CH CH Et Cl CF₃ Br CH N CH CH i-Pr Cl CF₃ Br CH N CH CH t-Bu Cl CF₃ Br CH N CH CH Et Cl CF₃ I CH N CH CH i-Pr Cl CF₃ I CH N CH CH t-Bu Cl CF₃ I CH N CH CH Et Cl CF₃ F CH N CH CH i-Pr Cl CF₃ F CH N CH CH t-Bu Cl CF₃ F CH N CH CH Et Cl CF₃ Me CH N CH CH i-Pr Cl CF₃ Me CH N CH CH t-Bu Cl CF₃ Me CH N CH CH Et Cl CF₃ CF₃ CH N CH CH i-Pr Cl CF₃ CF₃ CH N CH CH t-Bu Cl CF₃ CF₃ CH N CH CH Et Cl CF₃ OMe CH N CH CH i-Pr Cl CF₃ OMe CH N CH CH t-Bu Cl CF₃ OMe CH N CH CH Et Cl CF₃ CN CH N CH CH i-Pr Cl CF₃ CN CH N CH CH t-Bu Cl CF₃ CN N CH CH CH Et Me CF₃ Cl N CH CH CH i-Pr Me CF₃ Cl N CH CH CH t-Bu Me CF₃ Cl N CH CH CH Et Me CF₃ Br N CH CH CH i-Pr Me CF₃ Br N CH CH CH t-Bu Me CF₃ Br N CH CH CH Et Me CF₃ I N CH CH CH i-Pr Me CF₃ I N CH CH CH t-Bu Me CF₃ I N CH CH CH Et Me CF₃ F N CH CH CH i-Pr Me CF₃ F N CH CH CH t-Bu Me CF₃ F N CH CH CH Et Me CF₃ Me N CH CH CH i-Pr Me CF₃ Me N CH CH CH t-Bu Me CF₃ Me N CH CH CH Et Me CF₃ CF₃ N CH CH CH i-Pr Me CF₃ CF₃ N CH CH CH t-Bu Me CF₃ CF₃ N CH CH CH Et Me CF₃ OMe N CH CH CH i-Pr Me CF₃ OMe N CH CH CH t-Bu Me CF₃ OMe N CH CH CH Et Me CF₃ CN N CH CH CH i-Pr Me CF₃ CN N CH CH CH t-Bu Me CF₃ CN N CH CH CH Et Cl CF₃ Cl N CH CH CH i-Pr Cl CF₃ Cl N CH CH CH t-Bu Cl CF₃ Cl N CH CH CH Et Cl CF₃ Br N CH CH CH i-Pr Cl CF₃ Br N CH CH CH t-Bu Cl CF₃ Br N CH CH CH Et Cl CF₃ I N CH CH CH i-Pr Cl CF₃ I N CH CH CH t-Bu Cl CF₃ I N CH CH CH Et Cl CF₃ F N CH CH CH i-Pr Cl CF₃ F N CH CH CH t-Bu Cl CF₃ F N CH CH CH Et Cl CF₃ Me N CH CH CH i-Pr Cl CF₃ Me N CH CH CH t-Bu Cl CF₃ Me N CH CH CH Et Cl CF₃ CF₃ N CH CH CH i-Pr Cl CF₃ CF₃ N CH CH CH t-Bu Cl CF₃ CF₃ N CH CH CH Et Cl CF₃ OMe N CH CH CH i-Pr Cl CF₃ OMe N CH CH CH t-Bu Cl CF₃ OMe N CH CH CH Et Cl CF₃ CN N CH CH CH i-Pr Cl CF₃ CN N CH CH CH t-Bu Cl CF₃ CN CH N CH N Et Me CF₃ Cl CH N CH N i-Pr Me CF₃ Cl CH N CH N t-Bu Me CF₃ Cl CH N CH N Et Me CF₃ Br CH N CH N i-Pr Me CF₃ Br CH N CH N t-Bu Me CF₃ Br CH N CH N Et Me CF₃ I CH N CH N i-Pr Me CF₃ I CH N CH N t-Bu Me CF₃ I CH N CH N Et Me CF₃ F CH N CH N i-Pr Me CF₃ F CH N CH N t-Bu Me CF₃ F CH N CH N Et Me CF₃ Me CH N CH N i-Pr Me CF₃ Me CH N CH N t-Bu Me CF₃ Me CH N CH N Et Me CF₃ CF₃ CH N CH N i-Pr Me CF₃ CF₃ CH N CH N t-Bu Me CF₃ CF₃ CH N CH N Et Me CF₃ OMe CH N CH N i-Pr Me CF₃ OMe CH N CH N t-Bu Me CF₃ OMe CH N CH N Et Me CF₃ CN CH N CH N i-Pr Me CF₃ CN CH N CH N t-Bu Me CF₃ CN CH N CH N Et Cl CF₃ Cl CH N CH N i-Pr Cl CF₃ Cl CH N CH N t-Bu Cl CF₃ Cl CH N CH N Et Cl CF₃ Br CH N CH N i-Pr Cl CF₃ Br CH N CH N t-Bu Cl CF₃ Br CH N CH N Et Cl CF₃ I CH N CH N i-Pr Cl CF₃ I CH N CH N t-Bu Cl CF₃ I CH N CH N Et Cl CF₃ F CH N CH N i-Pr Cl CF₃ F CH N CH N t-Bu Cl CF₃ F CH N CH N Et Cl CF₃ Me CH N CH N i-Pr Cl CF₃ Me CH N CH N t-Bu Cl CF₃ Me CH N CH N Et Cl CF₃ CF₃ CH N CH N i-Pr Cl CF₃ CF₃ CH N CH N t-Bu Cl CF₃ CF₃ CH N CH N Et Cl CF₃ OMe CH N CH N i-Pr Cl CF₃ OMe CH N CH N t-Bu Cl CF₃ OMe CH N CH N Et Cl CF₃ CN CH N CH N i-Pr Cl CF₃ CN CH N CH N t-Bu Cl CF₃ CN CH CH CH CCl Et Me CF₃ Cl CH CH CH CCl i-Pr Me CF₃ Cl CH CH CH CCl t-Bu Me CF₃ Cl CH CH CH CCl Et Me CF₃ Br CH CH CH CCl i-Pr Me CF₃ Br CH CH CH CCl t-Bu Me CF₃ Br CH CH CH CCl Et Me CF₃ I CH CH CH CCl i-Pr Me CF₃ I CH CH CH CCl t-Bu Me CF₃ I CH CH CH CCl Et Me CF₃ F CH CH CH CCl i-Pr Me CF₃ F CH CH CH CCl t-Bu Me CF₃ F CH CH CH CCl Et Me CF₃ Me CH CH CH CCl i-Pr Me CF₃ Me CH CH CH CCl t-Bu Me CF₃ Me CH CH CH CCl Et Me CF₃ CF₃ CH CH CH CCl i-Pr Me CF₃ CF₃ CH CH CH CCl t-Bu Me CF₃ CF₃ CH CH CH CCl Et Me CF₃ OMe CH CH CH CCl i-Pr Me CF₃ OMe CH CH CH CCl t-Bu Me CF₃ OMe CH CH CH CCl Et Me CF₃ CN CH CH CH CCl i-Pr Me CF₃ CN CH CH CH CCl t-Bu Me CF₃ CN CH CH CH CCl Et Cl CF₃ Cl CH CH CH CCl i-Pr Cl CF₃ Cl CH CH CH CCl t-Bu Cl CF₃ Cl CH CH CH CCl Et Cl CF₃ Br CH CH CH CCl i-Pr Cl CF₃ Br CH CH CH CCl t-Bu Cl CF₃ Br CH CH CH CCl Et Cl CF₃ I CH CH CH CCl i-Pr Cl CF₃ I CH CH CH CCl t-Bu Cl CF₃ I CH CH CH CCl Et Cl CF₃ F CH CH CH CCl i-Pr Cl CF₃ F CH CH CH CCl t-Bu Cl CF₃ F CH CH CH CCl Et Cl CF₃ Me CH CH CH CCl i-Pr Cl CF₃ Me CH CH CH CCl t-Bu Cl CF₃ Me CH CH CH CCl Et Cl CF₃ CF₃ CH CH CH CCl i-Pr Cl CF₃ CF₃ CH CH CH CCl t-Bu Cl CF₃ CF₃ CH CH CH CCl Et Cl CF₃ OMe CH CH CH CCl i-Pr Cl CF₃ OMe CH CH CH CCl t-Bu Cl CF₃ OMe CH CH CH CCl Et Cl CF₃ CN CH CH CH CCl i-Pr Cl CF₃ CN CH CH CH CCl t-Bu Cl CF₃ CN CH CH CH CF Et Me CF₃ Cl CH CH CH CF i-Pr Me CF₃ Cl CH CH CH CF t-Bu Me CF₃ Cl CH CH CH CF Et Me CF₃ Br CH CH CH CF i-Pr Me CF₃ Br CH CH CH CF t-Bu Me CF₃ Br CH CH CH CF Et Me CF₃ I CH CH CH CF i-Pr Me CF₃ I CH CH CH CF t-Bu Me CF₃ I CH CH CH CF Et Me CF₃ F CH CH CH CF i-Pr Me CF₃ F CH CH CH CF t-Bu Me CF₃ F CH CH CH CF Et Me CF₃ Me CH CH CH CF i-Pr Me CF₃ Me CH CH CH CF t-Bu Me CF₃ Me CH CH CH CF Et Me CF₃ CF₃ CH CH CH CF i-Pr Me CF₃ CF₃ CH CH CH CF t-Bu Me CF₃ CF₃ CH CH CH CF Et Me CF₃ OMe CH CH CH CF i-Pr Me CF₃ OMe CH CH CH CF t-Bu Me CF₃ OMe CH CH CH CF Et Me CF₃ CN CH CH CH CF i-Pr Me CF₃ CN CH CH CH CF t-Bu Me CF₃ CN CH CH CH CF Et Cl CF₃ Cl CH CH CH CF i-Pr Cl CF₃ Cl CH CH CH CF t-Bu Cl CF₃ Cl CH CH CH CF Et Cl CF₃ Br CH CH CH CF i-Pr Cl CF₃ Br CH CH CH CF t-Bu Cl CF₃ Br CH CH CH CF Et Cl CF₃ I CH CH CH CF i-Pr Cl CF₃ I CH CH CH CF t-Bu Cl CF₃ I CH CH CH CF i-Pr Cl CF₃ F CH CH CH CF t-Bu Cl CF₃ F CH CH CH CF Et Cl CF₃ Me CH CH CH CF i-Pr Cl CF₃ Me CH CH CH CF t-Bu Cl CF₃ Me CH CH CH CF Et Cl CF₃ CF₃ CH CH CH CF i-Pr Cl CF₃ CF₃ CH CH CH CF t-Bu Cl CF₃ CF₃ CH CH CH CF Et Cl CF₃ OMe CH CH CH CF i-Pr Cl CF₃ OMe CH CH CH CF t-Bu Cl CF₃ OMe CH CH CH CF Et Cl CF₃ CN CH CH CH CF i-Pr Cl CF₃ CN CH CH CH CF t-Bu Cl CF₃ CN CH CH CH CH Et Me C₂F₅ Cl CH CH CH CH i-Pr Me C₂F₅ Cl CH CH CH CH t-Bu Me C₂F₅ Cl CH CH CH CH Et Me C₂F₅ Br CH CH CH CH i-Pr Me C₂F₅ Br CH CH CH CH t-Bu Me C₂F₅ Br CH CH CH CH Et Me C₂F₅ I CH CH CH CH i-Pr Me C₂F₅ I CH CH CH CH t-Bu Me C₂F₅ I CH CH CH CH Et Me C₂F₅ F CH CH CH CH i-Pr Me C₂F₅ F CH CH CH CH t-Bu Me C₂F₅ F CH CH CH CH Et Me C₂F₅ Me CH CH CH CH i-Pr Me C₂F₅ Me CH CH CH CH t-Bu Me C₂F₅ Me CH CH CH CH Et Me C₂F₅ CF₃ CH CH CH CH i-Pr Me C₂F₅ CF₃ CH CH CH CH t-Bu Me C₂F₅ CF₃ CH CH CH CH Et Me C₂F₅ OMe CH CH CH CH i-Pr Me C₂F₅ OMe CH CH CH CH t-Bu Me C₂F₅ OMe CH CH CH CH Et Me C₂F₅ CN CH CH CH CH i-Pr Me C₂F₅ CN CH CH CH CH t-Bu Me C₂F₅ CN CH CH CH CH Et Cl C₂F₅ Cl CH CH CH CH i-Pr Cl C₂F₅ Cl CH CH CH CH t-Bu Cl C₂F₅ Cl CH CH CH CH Et Cl C₂F₅ Br CH CH CH CH i-Pr Cl C₂F₅ Br CH CH CH CH t-Bu Cl C₂F₅ Br CH CH CH CH Et Cl C₂F₅ I CH CH CH CH i-Pr Cl C₂F₅ I CH CH CH CH t-Bu Cl C₂F₅ I CH CH CH CH Et Cl C₂F₅ F CH CH CH CH i-Pr Cl C₂F₅ F CH CH CH CH t-Bu Cl C₂F₅ F CH CH CH CH Et Cl C₂F₅ Me CH CH CH CH i-Pr Cl C₂F₅ Me CH CH CH CH t-Bu Cl C₂F₅ Me CH CH CH CH Et Cl C₂F₅ CF₃ CH CH CH CH i-Pr Cl C₂F₅ CF₃ CH CH CH CH t-Bu Cl C₂F₅ CF₃ CH CH CH CH Et Cl C₂F₅ OMe CH CH CH CH i-Pr Cl C₂F₅ OMe CH CH CH CH t-Bu Cl C₂F₅ OMe CH CH CH CH Et Cl C₂F₅ CN CH CH CH CH i-Pr Cl C₂F₅ CN CH CH CH CH t-Bu Cl C₂F₅ CN

TABLE 15

W X Y Z R³ R⁴ R⁷ R⁸ CH CH CH CH Et Me CF₃ Cl CH CH CH CH i-Pr Me CF₃ Cl CH CH CH CH t-Bu Me CF₃ Cl CH CH CH CH Et Me CF₃ Br CH CH CH CH i-Pr Me CF₃ Br CH CH CH CH t-Bu Me CF₃ Br CH CH CH CH Et Me CF₃ I CH CH CH CH i-Pr Me CF₃ I CH CH CH CH t-Bu Me CF₃ I CH CH CH CH Et Me CF₃ F CH CH CH CH i-Pr Me CF₃ F CH CH CH CH t-Bu Me CF₃ F CH CH CH CH Et Me CF₃ Me CH CH CH CH i-Pr Me CF₃ Me CH CH CH CH t-Bu Me CF₃ Me CH CH CH CH Et Me CF₃ CF₃ CH CH CH CH i-Pr Me CF₃ CF₃ CH CH CH CH t-Bu Me CF₃ CF₃ CH CH CH CH Et Me CF₃ OMe CH CH CH CH i-Pr Me CF₃ OMe CH CH CH CH t-Bu Me CF₃ OMe CH CH CH CH Et Me CF₃ CN CH CH CH CH i-Pr Me CF₃ CN CH CH CH CH t-Bu Me CF₃ CN CH CH CH CH Et Cl CF₃ Cl CH CH CH CH i-Pr Cl CF₃ Cl CH CH CH CH t-Bu Cl CF₃ Cl CH CH CH CH Et Cl CF₃ Br CH CH CH CH i-Pr Cl CF₃ Br CH CH CH CH t-Bu Cl CF₃ Br CH CH CH CH Et Cl CF₃ I CH CH CH CH i-Pr Cl CF₃ I CH CH CH CH t-Bu Cl CF₃ I CH CH CH CH Et Cl CF₃ F CH CH CH CH i-Pr Cl CF₃ F CH CH CH CH t-Bu Cl CF₃ F CH CH CH CH Et Cl CF₃ Me CH CH CH CH i-Pr Cl CF₃ Me CH CH CH CH t-Bu Cl CF₃ Me CH CH CH CH Et Cl CF₃ CF₃ CH CH CH CH i-Pr Cl CF₃ CF₃ CH CH CH CH t-Bu Cl CF₃ CF₃ CH CH CH CH Et Cl CF₃ OMe CH CH CH CH i-Pr Cl CF₃ OMe CH CH CH CH t-Bu Cl CF₃ OMe CH CH CH CH Et Cl CF₃ CN CH CH CH CH i-Pr Cl CF₃ CN CH CH CH CH t-Bu Cl CF₃ CN CH CH CH N Et Me CF₃ Cl CH CH CH N i-Pr Me CF₃ Cl CH CH CH N t-Bu Me CF₃ Cl CH CH CH N Et Me CF₃ Br CH CH CH N i-Pr Me CF₃ Br CH CH CH N t-Bu Me CF₃ Br CH CH CH N Et Me CF₃ I CH CH CH N i-Pr Me CF₃ I CH CH CH N t-Bu Me CF₃ I CH CH CH N Et Me CF₃ F CH CH CH N i-Pr Me CF₃ F CH CH CH N t-Bu Me CF₃ F CH CH CH N Et Me CF₃ Me CH CH CH N i-Pr Me CF₃ Me CH CH CH N t-Bu Me CF₃ Me CH CH CH N Et Me CF₃ CF₃ CH CH CH N i-Pr Me CF₃ CF₃ CH CH CH N t-Bu Me CF₃ CF₃ CH CH CH N Et Me CF₃ OMe CH CH CH N i-Pr Me CF₃ OMe CH CH CH N t-Bu Me CF₃ OMe CH CH CH N Et Me CF₃ CN CH CH CH N i-Pr Me CF₃ CN CH CH CH N t-Bu Me CF₃ CN CH CH CH N Et Cl CF₃ Cl CH CH CH N i-Pr Cl CF₃ Cl CH CH CH N t-Bu Cl CF₃ Cl CH CH CH N Et Cl CF₃ Br CH CH CH N i-Pr Cl CF₃ Br CH CH CH N t-Bu Cl CF₃ Br CH CH CH N Et Cl CF₃ I CH CH CH N i-Pr Cl CF₃ I CH CH CH N t-Bu Cl CF₃ I CH CH CH N Et Cl CF₃ F CH CH CH N i-Pr Cl CF₃ F CH CH CH N t-Bu Cl CF₃ F CH CH CH N Et Cl CF₃ Me CH CH CH N i-Pr Cl CF₃ Me CH CH CH N t-Bu Cl CF₃ Me CH CH CH N Et Cl CF₃ CF₃ CH CH CH N i-Pr Cl CF₃ CF₃ CH CH CH N t-Bu Cl CF₃ CF₃ CH CH CH N Et Cl CF₃ OMe CH CH CH N i-Pr Cl CF₃ OMe CH CH CH N t-Bu Cl CF₃ OMe CH CH CH N Et Cl CF₃ CN CH CH CH N i-Pr Cl CF₃ CN CH CH CH N t-Bu Cl CF₃ CN CH CH N CH Et Me CF₃ Cl CH CH N CH i-Pr Me CF₃ Cl CH CH N CH t-Bu Me CF₃ Cl CH CH N CH Et Me CF₃ Br CH CH N CH i-Pr Me CF₃ Br CH CH N CH t-Bu Me CF₃ Br CH CH N CH Et Me CF₃ I CH CH N CH i-Pr Me CF₃ I CH CH N CH t-Bu Me CF₃ I CH CH N CH Et Me CF₃ F CH CH N CH i-Pr Me CF₃ F CH CH N CH t-Bu Me CF₃ F CH CH N CH Et Me CF₃ Me CH CH N CH i-Pr Me CF₃ Me CH CH N CH t-Bu Me CF₃ Me CH CH N CH Et Me CF₃ CF₃ CH CH N CH i-Pr Me CF₃ CF₃ CH CH N CH t-Bu Me CF₃ CF₃ CH CH N CH Et Me CF₃ OMe CH CH N CH i-Pr Me CF₃ OMe CH CH N CH t-Bu Me CF₃ OMe CH CH N CH Et Me CF₃ CN CH CH N CH i-Pr Me CF₃ CN CH CH N CH t-Bu Me CF₃ CN CH CH N CH Et Cl CF₃ Cl CH CH N CH i-Pr Cl CF₃ Cl CH CH N CH t-Bu Cl CF₃ Cl CH CH N CH Et Cl CF₃ Br CH CH N CH i-Pr Cl CF₃ Br CH CH N CH t-Bu Cl CF₃ Br CH CH N CH Et Cl CF₃ I CH CH N CH i-Pr Cl CF₃ I CH CH N CH t-Bu Cl CF₃ I CH CH N CH Et Cl CF₃ F CH CH N CH i-Pr Cl CF₃ F CH CH N CH t-Bu Cl CF₃ F CH CH N CH Et Cl CF₃ Me CH CH N CH i-Pr Cl CF₃ Me CH CH N CH t-Bu Cl CF₃ Me CH CH N CH Et Cl CF₃ CF₃ CH CH N CH i-Pr Cl CF₃ CF₃ CH CH N CH t-Bu Cl CF₃ CF₃ CH CH N CH Et Cl CF₃ OMe CH CH N CH i-Pr Cl CF₃ OMe CH CH N CH t-Bu Cl CF₃ OMe CH CH N CH Et Cl CF₃ CN CH CH N CH i-Pr Cl CF₃ CN CH CH N CH t-Bu Cl CF₃ CN CH N CH CH Et Me CF₃ Cl CH N CH CH i-Pr Me CF₃ Cl CH N CH CH t-Bu Me CF₃ Cl CH N CH CH Et Me CF₃ Br CH N CH CH i-Pr Me CF₃ Br CH N CH CH t-Bu Me CF₃ Br CH N CH CH Et Me CF₃ I CH N CH CH i-Pr Me CF₃ I CH N CH CH t-Bu Me CF₃ I CH N CH CH Et Me CF₃ F CH N CH CH i-Pr Me CF₃ F CH N CH CH t-Bu Me CF₃ F CH N CH CH Et Me CF₃ Me CH N CH CH i-Pr Me CF₃ Me CH N CH CH t-Bu Me CF₃ Me CH N CH CH Et Me CF₃ CF₃ CH N CH CH i-Pr Me CF₃ CF₃ CH N CH CH t-Bu Me CF₃ CF₃ CH N CH CH Et Me CF₃ OMe CH N CH CH i-Pr Me CF₃ OMe CH N CH CH t-Bu Me CF₃ OMe CH N CH CH Et Me CF₃ CN CH N CH CH i-Pr Me CF₃ CN CH N CH CH t-Bu Me CF₃ CN CH N CH CH Et Cl CF₃ Cl CH N CH CH i-Pr Cl CF₃ Cl CH N CH CH t-Bu Cl CF₃ Cl CH N CH CH Et Cl CF₃ Br CH N CH CH i-Pr Cl CF₃ Br CH N CH CH t-Bu Cl CF₃ Br CH N CH CH Et Cl CF₃ I CH N CH CH i-Pr Cl CF₃ I CH N CH CH t-Bu Cl CF₃ I CH N CH CH Et Cl CF₃ F CH N CH CH i-Pr Cl CF₃ F CH N CH CH t-Bu Cl CF₃ F CH N CH CH Et Cl CF₃ Me CH N CH CH i-Pr Cl CF₃ Me CH N CH CH t-Bu Cl CF₃ Me CH N CH CH Et Cl CF₃ CF₃ CH N CH CH i-Pr Cl CF₃ CF₃ CH N CH CH t-Bu Cl CF₃ CF₃ CH N CH CH Et Cl CF₃ OMe CH N CH CH i-Pr Cl CF₃ OMe CH N CH CH t-Bu Cl CF₃ OMe CH N CH CH Et Cl CF₃ CN CH N CH CH i-Pr Cl CF₃ CN CH N CH CH t-Bu Cl CF₃ CN N CH CH CH Et Me CF₃ Cl N CH CH CH i-Pr Me CF₃ Cl N CH CH CH t-Bu Me CF₃ Cl N CH CH CH Et Me CF₃ Br N CH CH CH i-Pr Me CF₃ Br N CH CH CH t-Bu Me CF₃ Br N CH CH CH Et Me CF₃ I N CH CH CH i-Pr Me CF₃ I N CH CH CH t-Bu Me CF₃ I N CH CH CH Et Me CF₃ F N CH CH CH i-Pr Me CF₃ F N CH CH CH t-Bu Me CF₃ F N CH CH CH Et Me CF₃ Me N CH CH CH i-Pr Me CF₃ Me N CH CH CH t-Bu Me CF₃ Me N CH CH CH Et Me CF₃ CF₃ N CH CH CH i-Pr Me CF₃ CF₃ N CH CH CH t-Bu Me CF₃ CF₃ N CH CH CH Et Me CF₃ OMe N CH CH CH i-Pr Me CF₃ OMe N CH CH CH t-Bu Me CF₃ OMe N CH CH CH Et Me CF₃ CN N CH CH CH i-Pr Me CF₃ CN N CH CH CH t-Bu Me CF₃ CN N CH CH CH Et Cl CF₃ Cl N CH CH CH i-Pr Cl CF₃ Cl N CH CH CH t-Bu Cl CF₃ Cl N CH CH CH Et Cl CF₃ Br N CH CH CH i-Pr Cl CF₃ Br N CH CH CH t-Bu Cl CF₃ Br N CH CH CH Et Cl CF₃ I N CH CH CH i-Pr Cl CF₃ I N CH CH CH t-Bu Cl CF₃ I N CH CH CH Et Cl CF₃ F N CH CH CH i-Pr Cl CF₃ F N CH CH CH t-Bu Cl CF₃ F N CH CH CH Et Cl CF₃ Me N CH CH CH i-Pr Cl CF₃ Me N CH CH CH t-Bu Cl CF₃ Me N CH CH CH Et Cl CF₃ CF₃ N CH CH CH i-Pr Cl CF₃ CF₃ N CH CH CH t-Bu Cl CF₃ CF₃ N CH CH CH Et Cl CF₃ OMe N CH CH CH i-Pr Cl CF₃ OMe N CH CH CH t-Bu Cl CF₃ OMe N CH CH CH Et Cl CF₃ CN N CH CH CH i-Pr Cl CF₃ CN N CH CH CH t-Bu Cl CF₃ CN CH N CH N Et Me CF₃ Cl CH N CH N i-Pr Me CF₃ Cl CH N CH N t-Bu Me CF₃ Cl CH N CH N Et Me CF₃ Br CH N CH N i-Pr Me CF₃ Br CH N CH N t-Bu Me CF₃ Br CH N CH N Et Me CF₃ I CH N CH N i-Pr Me CF₃ I CH N CH N t-Bu Me CF₃ I CH N CH N Et Me CF₃ F CH N CH N i-Pr Me CF₃ F CH N CH N t-Bu Me CF₃ F CH N CH N Et Me CF₃ Me CH N CH N i-Pr Me CF₃ Me CH N CH N t-Bu Me CF₃ Me CH N CH N Et Me CF₃ CF₃ CH N CH N i-Pr Me CF₃ CF₃ CH N CH N t-Bu Me CF₃ CF₃ CH N CH N Et Me CF₃ OMe CH N CH N i-Pr Me CF₃ OMe CH N CH N t-Bu Me CF₃ OMe CH N CH N Et Me CF₃ CN CH N CH N i-Pr Me CF₃ CN CH N CH N t-Bu Me CF₃ CN CH N CH N Et Cl CF₃ Cl CH N CH N i-Pr Cl CF₃ Cl CH N CH N t-Bu Cl CF₃ Cl CH N CH N Et Cl CF₃ Br CH N CH N i-Pr Cl CF₃ Br CH N CH N t-Bu Cl CF₃ Br CH N CH N Et Cl CF₃ I CH N CH N i-Pr Cl CF₃ I CH N CH N t-Bu Cl CF₃ I CH N CH N Et Cl CF₃ F CH N CH N i-Pr Cl CF₃ F CH N CH N t-Bu Cl CF₃ F CH N CH N Et Cl CF₃ Me CH N CH N i-Pr Cl CF₃ Me CH N CH N t-Bu Cl CF₃ Me CH N CH N Et Cl CF₃ CF₃ CH N CH N i-Pr Cl CF₃ CF₃ CH N CH N t-Bu Cl CF₃ CF₃ CH N CH N Et Cl CF₃ OMe CH N CH N i-Pr Cl CF₃ OMe CH N CH N t-Bu Cl CF₃ OMe CH N CH N Et Cl CF₃ CN CH N CH N i-Pr Cl CF₃ CN CH N CH N t-Bu Cl CF₃ CN CH CH CH CCl Et Me CF₃ Cl CH CH CH CCl i-Pr Me CF₃ Cl CH CH CH CCl t-Bu Me CF₃ Cl CH CH CH CCl Et Me CF₃ Br CH CH CH CCl i-Pr Me CF₃ Br CH CH CH CCl t-Bu Me CF₃ Br CH CH CH CCl Et Me CF₃ I CH CH CH CCl i-Pr Me CF₃ I CH CH CH CCl t-Bu Me CF₃ I CH CH CH CCl Et Me CF₃ F CH CH CH CCl i-Pr Me CF₃ F CH CH CH CCl t-Bu Me CF₃ F CH CH CH CCl Et Me CF₃ Me CH CH CH CCl i-Pr Me CF₃ Me CH CH CH CCl t-Bu Me CF₃ Me CH CH CH CCl Et Me CF₃ CF₃ CH CH CH CCl i-Pr Me CF₃ CF₃ CH CH CH CCl t-Bu Me CF₃ CF₃ CH CH CH CCl Et Me CF₃ OMe CH CH CH CCl i-Pr Me CF₃ OMe CH CH CH CCl t-Bu Me CF₃ OMe CH CH CH CCl Et Me CF₃ CN CH CH CH CCl i-Pr Me CF₃ CN CH CH CH CCl t-Bu Me CF₃ CN CH CH CH CCl Et Cl CF₃ Cl CH CH CH CCl i-Pr Cl CF₃ Cl CH CH CH CCl t-Bu Cl CF₃ Cl CH CH CH CCl Et Cl CF₃ Br CH CH CH CCl i-Pr Cl CF₃ Br CH CH CH CCl t-Bu Cl CF₃ Br CH CH CH CCl Et Cl CF₃ I CH CH CH CCl i-Pr Cl CF₃ I CH CH CH CCl t-Bu Cl CF₃ I CH CH CH CCl Et Cl CF₃ F CH CH CH CCl i-Pr Cl CF₃ F CH CH CH CCl t-Bu Cl CF₃ F CH CH CH CCl Et Cl CF₃ Me CH CH CH CCl i-Pr Cl CF₃ Me CH CH CH CCl t-Bu Cl CF₃ Me CH CH CH CCl Et Cl CF₃ CF₃ CH CH CH CCl i-Pr Cl CF₃ CF₃ CH CH CH CCl t-Bu Cl CF₃ CF₃ CH CH CH CCl Et Cl CF₃ OMe CH CH CH CCl i-Pr Cl CF₃ OMe CH CH CH CCl t-Bu Cl CF₃ OMe CH CH CH CCl Et Cl CF₃ CN CH CH CH CCl i-Pr Cl CF₃ CN CH CH CH CCl t-Bu Cl CF₃ CN CH CH CH CF Et Me CF₃ Cl CH CH CH CF i-Pr Me CF₃ Cl CH CH CH CF t-Bu Me CF₃ Cl CH CH CH CF Et Me CF₃ Br CH CH CH CF i-Pr Me CF₃ Br CH CH CH CF t-Bu Me CF₃ Br CH CH CH CF Et Me CF₃ I CH CH CH CF i-Pr Me CF₃ I CH CH CH CF t-Bu Me CF₃ I CH CH CH CF Et Me CF₃ F CH CH CH CF i-Pr Me CF₃ F CH CH CH CF t-Bu Me CF₃ F CH CH CH CF Et Me CF₃ Me CH CH CH CF i-Pr Me CF₃ Me CH CH CH CF t-Bu Me CF₃ Me CH CH CH CF Et Me CF₃ CF₃ CH CH CH CF i-Pr Me CF₃ CF₃ CH CH CH CF t-Bu Me CF₃ CF₃ CH CH CH CF Et Me CF₃ OMe CH CH CH CF i-Pr Me CF₃ OMe CH CH CH CF t-Bu Me CF₃ OMe CH CH CH CF Et Me CF₃ CN CH CH CH CF i-Pr Me CF₃ CN CH CH CH CF t-Bu Me CF₃ CN CH CH CH CF Et Cl CF₃ Cl CH CH CH CF i-Pr Cl CF₃ Cl CH CH CH CF t-Bu Cl CF₃ Cl CH CH CH CF Et Cl CF₃ Br CH CH CH CF i-Pr Cl CF₃ Br CH CH CH CF t-Bu Cl CF₃ Br CH CH CH CF Et Cl CF₃ I CH CH CH CF i-Pr Cl CF₃ I CH CH CH CF t-Bu Cl CF₃ I CH CH CH CF i-Pr Cl CF₃ F CH CH CH CF t-Bu Cl CF₃ F CH CH CH CF Et Cl CF₃ Me CH CH CH CF i-Pr Cl CF₃ Me CH CH CH CF t-Bu Cl CF₃ Me CH CH CH CF Et Cl CF₃ CF₃ CH CH CH CF i-Pr Cl CF₃ CF₃ CH CH CH CF t-Bu Cl CF₃ CF₃ CH CH CH CF Et Cl CF₃ OMe CH CH CH CF i-Pr Cl CF₃ OMe CH CH CH CF t-Bu Cl CF₃ OMe CH CH CH CF Et Cl CF₃ CN CH CH CH CF i-Pr Cl CF₃ CN CH CH CH CF t-Bu Cl CF₃ CN CH CH CH CH Et Me C₂F₅ Cl CH CH CH CH i-Pr Me C₂F₅ Cl CH CH CH CH t-Bu Me C₂F₅ Cl CH CH CH CH Et Me C₂F₅ Br CH CH CH CH i-Pr Me C₂F₅ Br CH CH CH CH t-Bu Me C₂F₅ Br CH CH CH CH Et Me C₂F₅ I CH CH CH CH i-Pr Me C₂F₅ I CH CH CH CH t-Bu Me C₂F₅ I CH CH CH CH Et Me C₂F₅ F CH CH CH CH i-Pr Me C₂F₅ F CH CH CH CH t-Bu Me C₂F₅ F CH CH CH CH Et Me C₂F₅ Me CH CH CH CH i-Pr Me C₂F₅ Me CH CH CH CH t-Bu Me C₂F₅ Me CH CH CH CH Et Me C₂F₅ CF₃ CH CH CH CH i-Pr Me C₂F₅ CF₃ CH CH CH CH t-Bu Me C₂F₅ CF₃ CH CH CH CH Et Me C₂F₅ OMe CH CH CH CH i-Pr Me C₂F₅ OMe CH CH CH CH t-Bu Me C₂F₅ OMe CH CH CH CH Et Me C₂F₅ CN CH CH CH CH i-Pr Me C₂F₅ CN CH CH CH CH t-Bu Me C₂F₅ CN CH CH CH CH Et Cl C₂F₅ Cl CH CH CH CH i-Pr Cl C₂F₅ Cl CH CH CH CH t-Bu Cl C₂F₅ Cl CH CH CH CH Et Cl C₂F₅ Br CH CH CH CH i-Pr Cl C₂F₅ Br CH CH CH CH t-Bu Cl C₂F₅ Br CH CH CH CH Et Cl C₂F₅ I CH CH CH CH i-Pr Cl C₂F₅ I CH CH CH CH t-Bu Cl C₂F₅ I CH CH CH CH Et Cl C₂F₅ F CH CH CH CH i-Pr Cl C₂F₅ F CH CH CH CH t-Bu Cl C₂F₅ F CH CH CH CH Et Cl C₂F₅ Me CH CH CH CH i-Pr Cl C₂F₅ Me CH CH CH CH t-Bu Cl C₂F₅ Me CH CH CH CH Et Cl C₂F₅ CF₃ CH CH CH CH i-Pr Cl C₂F₅ CF₃ CH CH CH CH t-Bu Cl C₂F₅ CF₃ CH CH CH CH Et Cl C₂F₅ OMe CH CH CH CH i-Pr Cl C₂F₅ OMe CH CH CH CH t-Bu Cl C₂F₅ OMe CH CH CH CH Et Cl C₂F₅ CN CH CH CH CH i-Pr Cl C₂F₅ CN CH CH CH CH t-Bu Cl C₂F₅ CN

TABLE 16

W X Y Z R³ R⁴ R⁷ R⁸ CH CH CH CH Et Me CF₃ Cl CH CH CH CH i-Pr Me CF₃ Cl CH CH CH CH t-Bu Me CF₃ Cl CH CH CH CH Et Me CF₃ Br CH CH CH CH i-Pr Me CF₃ Br CH CH CH CH t-Bu Me CF₃ Br CH CH CH CH Et Me CF₃ I CH CH CH CH i-Pr Me CF₃ I CH CH CH CH t-Bu Me CF₃ I CH CH CH CH Et Me CF₃ F CH CH CH CH i-Pr Me CF₃ F CH CH CH CH t-Bu Me CF₃ F CH CH CH CH Et Me CF₃ Me CH CH CH CH i-Pr Me CF₃ Me CH CH CH CH t-Bu Me CF₃ Me CH CH CH CH Et Me CF₃ CF₃ CH CH CH CH i-Pr Me CF₃ CF₃ CH CH CH CH t-Bu Me CF₃ CF₃ CH CH CH CH Et Me CF₃ OMe CH CH CH CH i-Pr Me CF₃ OMe CH CH CH CH t-Bu Me CF₃ OMe CH CH CH CH Et Me CF₃ CN CH CH CH CH i-Pr Me CF₃ CN CH CH CH CH t-Bu Me CF₃ CN CH CH CH CH Et Cl CF₃ Cl CH CH CH CH i-Pr Cl CF₃ Cl CH CH CH CH t-Bu Cl CF₃ Cl CH CH CH CH Et Cl CF₃ Br CH CH CH CH i-Pr Cl CF₃ Br CH CH CH CH t-Bu Cl CF₃ Br CH CH CH CH Et Cl CF₃ I CH CH CH CH i-Pr Cl CF₃ I CH CH CH CH t-Bu Cl CF₃ I CH CH CH CH Et Cl CF₃ F CH CH CH CH i-Pr Cl CF₃ F CH CH CH CH t-Bu Cl CF₃ F CH CH CH CH Et Cl CF₃ Me CH CH CH CH i-Pr Cl CF₃ Me CH CH CH CH t-Bu Cl CF₃ Me CH CH CH CH Et Cl CF₃ CF₃ CH CH CH CH i-Pr Cl CF₃ CF₃ CH CH CH CH t-Bu Cl CF₃ CF₃ CH CH CH CH Et Cl CF₃ OMe CH CH CH CH i-Pr Cl CF₃ OMe CH CH CH CH t-Bu Cl CF₃ OMe CH CH CH CH Et Cl CF₃ CN CH CH CH CH i-Pr Cl CF₃ CN CH CH CH CH t-Bu Cl CF₃ CN CH CH CH N Et Me CF₃ Cl CH CH CH N i-Pr Me CF₃ Cl CH CH CH N t-Bu Me CF₃ Cl CH CH CH N Et Me CF₃ Br CH CH CH N i-Pr Me CF₃ Br CH CH CH N t-Bu Me CF₃ Br CH CH CH N Et Me CF₃ I CH CH CH N i-Pr Me CF₃ I CH CH CH N t-Bu Me CF₃ I CH CH CH N Et Me CF₃ F CH CH CH N i-Pr Me CF₃ F CH CH CH N t-Bu Me CF₃ F CH CH CH N Et Me CF₃ Me CH CH CH N i-Pr Me CF₃ Me CH CH CH N t-Bu Me CF₃ Me CH CH CH N Et Me CF₃ CF₃ CH CH CH N i-Pr Me CF₃ CF₃ CH CH CH N t-Bu Me CF₃ CF₃ CH CH CH N Et Me CF₃ OMe CH CH CH N i-Pr Me CF₃ OMe CH CH CH N t-Bu Me CF₃ OMe CH CH CH N Et Me CF₃ CN CH CH CH N i-Pr Me CF₃ CN CH CH CH N t-Bu Me CF₃ CN CH CH CH N Et Cl CF₃ Cl CH CH CH N i-Pr Cl CF₃ Cl CH CH CH N t-Bu Cl CF₃ Cl CH CH CH N Et Cl CF₃ Br CH CH CH N i-Pr Cl CF₃ Br CH CH CH N t-Bu Cl CF₃ Br CH CH CH N Et Cl CF₃ I CH CH CH N i-Pr Cl CF₃ I CH CH CH N t-Bu Cl CF₃ I CH CH CH N Et Cl CF₃ F CH CH CH N i-Pr Cl CF₃ F CH CH CH N t-Bu Cl CF₃ F CH CH CH N Et Cl CF₃ Me CH CH CH N i-Pr Cl CF₃ Me CH CH CH N t-Bu Cl CF₃ Me CH CH CH N Et Cl CF₃ CF₃ CH CH CH N i-Pr Cl CF₃ CF₃ CH CH CH N t-Bu Cl CF₃ CF₃ CH CH CH N Et Cl CF₃ OMe CH CH CH N i-Pr Cl CF₃ OMe CH CH CH N t-Bu Cl CF₃ OMe CH CH CH N Et Cl CF₃ CN CH CH CH N i-Pr Cl CF₃ CN CH CH CH N t-Bu Cl CF₃ CN CH CH N CH Et Me CF₃ Cl CH CH N CH i-Pr Me CF₃ Cl CH CH N CH t-Bu Me CF₃ Cl CH CH N CH Et Me CF₃ Br CH CH N CH i-Pr Me CF₃ Br CH CH N CH t-Bu Me CF₃ Br CH CH N CH Et Me CF₃ I CH CH N CH i-Pr Me CF₃ I CH CH N CH t-Bu Me CF₃ I CH CH N CH Et Me CF₃ F CH CH N CH i-Pr Me CF₃ F CH CH N CH t-Bu Me CF₃ F CH CH N CH Et Me CF₃ Me CH CH N CH i-Pr Me CF₃ Me CH CH N CH t-Bu Me CF₃ Me CH CH N CH Et Me CF₃ CF₃ CH CH N CH i-Pr Me CF₃ CF₃ CH CH N CH t-Bu Me CF₃ CF₃ CH CH N CH Et Me CF₃ OMe CH CH N CH i-Pr Me CF₃ OMe CH CH N CH t-Bu Me CF₃ OMe CH CH N CH Et Me CF₃ CN CH CH N CH i-Pr Me CF₃ CN CH CH N CH t-Bu Me CF₃ CN CH CH N CH Et Cl CF₃ Cl CH CH N CH i-Pr Cl CF₃ Cl CH CH N CH t-Bu Cl CF₃ Cl CH CH N CH Et Cl CF₃ Br CH CH N CH i-Pr Cl CF₃ Br CH CH N CH t-Bu Cl CF₃ Br CH CH N CH Et Cl CF₃ I CH CH N CH i-Pr Cl CF₃ I CH CH N CH t-Bu Cl CF₃ I CH CH N CH Et Cl CF₃ F CH CH N CH i-Pr Cl CF₃ F CH CH N CH t-Bu Cl CF₃ F CH CH N CH Et Cl CF₃ Me CH CH N CH i-Pr Cl CF₃ Me CH CH N CH t-Bu Cl CF₃ Me CH CH N CH Et Cl CF₃ CF₃ CH CH N CH i-Pr Cl CF₃ CF₃ CH CH N CH t-Bu Cl CF₃ CF₃ CH CH N CH Et Cl CF₃ OMe CH CH N CH i-Pr Cl CF₃ OMe CH CH N CH t-Bu Cl CF₃ OMe CH CH N CH Et Cl CF₃ CN CH CH N CH i-Pr Cl CF₃ CN CH CH N CH t-Bu Cl CF₃ CN CH N CH CH Et Me CF₃ Cl CH N CH CH i-Pr Me CF₃ Cl CH N CH CH t-Bu Me CF₃ Cl CH N CH CH Et Me CF₃ Br CH N CH CH i-Pr Me CF₃ Br CH N CH CH t-Bu Me CF₃ Br CH N CH CH Et Me CF₃ I CH N CH CH i-Pr Me CF₃ I CH N CH CH t-Bu Me CF₃ I CH N CH CH Et Me CF₃ F CH N CH CH i-Pr Me CF₃ F CH N CH CH t-Bu Me CF₃ F CH N CH CH Et Me CF₃ Me CH N CH CH i-Pr Me CF₃ Me CH N CH CH t-Bu Me CF₃ Me CH N CH CH Et Me CF₃ CF₃ CH N CH CH i-Pr Me CF₃ CF₃ CH N CH CH t-Bu Me CF₃ CF₃ CH N CH CH Et Me CF₃ OMe CH N CH CH i-Pr Me CF₃ OMe CH N CH CH t-Bu Me CF₃ OMe CH N CH CH Et Me CF₃ CN CH N CH CH i-Pr Me CF₃ CN CH N CH CH t-Bu Me CF₃ CN CH N CH CH Et Cl CF₃ Cl CH N CH CH i-Pr Cl CF₃ Cl CH N CH CH t-Bu Cl CF₃ Cl CH N CH CH Et Cl CF₃ Br CH N CH CH i-Pr Cl CF₃ Br CH N CH CH t-Bu Cl CF₃ Br CH N CH CH Et Cl CF₃ I CH N CH CH i-Pr Cl CF₃ I CH N CH CH t-Bu Cl CF₃ I CH N CH CH Et Cl CF₃ F CH N CH CH i-Pr Cl CF₃ F CH N CH CH t-Bu Cl CF₃ F CH N CH CH Et Cl CF₃ Me CH N CH CH i-Pr Cl CF₃ Me CH N CH CH t-Bu Cl CF₃ Me CH N CH CH Et Cl CF₃ CF₃ CH N CH CH i-Pr Cl CF₃ CF₃ CH N CH CH t-Bu Cl CF₃ CF₃ CH N CH CH Et Cl CF₃ OMe CH N CH CH i-Pr Cl CF₃ OMe CH N CH CH t-Bu Cl CF₃ OMe CH N CH CH Et Cl CF₃ CN CH N CH CH i-Pr Cl CF₃ CN CH N CH CH t-Bu Cl CF₃ CN N CH CH CH Et Me CF₃ Cl N CH CH CH i-Pr Me CF₃ Cl N CH CH CH t-Bu Me CF₃ Cl N CH CH CH Et Me CF₃ Br N CH CH CH i-Pr Me CF₃ Br N CH CH CH t-Bu Me CF₃ Br N CH CH CH Et Me CF₃ I N CH CH CH i-Pr Me CF₃ I N CH CH CH t-Bu Me CF₃ I N CH CH CH Et Me CF₃ F N CH CH CH i-Pr Me CF₃ F N CH CH CH t-Bu Me CF₃ F N CH CH CH Et Me CF₃ Me N CH CH CH i-Pr Me CF₃ Me N CH CH CH t-Bu Me CF₃ Me N CH CH CH Et Me CF₃ CF₃ N CH CH CH i-Pr Me CF₃ CF₃ N CH CH CH t-Bu Me CF₃ CF₃ N CH CH CH Et Me CF₃ OMe N CH CH CH i-Pr Me CF₃ OMe N CH CH CH t-Bu Me CF₃ OMe N CH CH CH Et Me CF₃ CN N CH CH CH i-Pr Me CF₃ CN N CH CH CH t-Bu Me CF₃ CN N CH CH CH Et Cl CF₃ Cl N CH CH CH i-Pr Cl CF₃ Cl N CH CH CH t-Bu Cl CF₃ Cl N CH CH CH Et Cl CF₃ Br N CH CH CH i-Pr Cl CF₃ Br N CH CH CH t-Bu Cl CF₃ Br N CH CH CH Et Cl CF₃ I N CH CH CH i-Pr Cl CF₃ I N CH CH CH t-Bu Cl CF₃ I N CH CH CH Et Cl CF₃ F N CH CH CH i-Pr Cl CF₃ F N CH CH CH t-Bu Cl CF₃ F N CH CH CH Et Cl CF₃ Me N CH CH CH i-Pr Cl CF₃ Me N CH CH CH t-Bu Cl CF₃ Me N CH CH CH Et Cl CF₃ CF₃ N CH CH CH i-Pr Cl CF₃ CF₃ N CH CH CH t-Bu Cl CF₃ CF₃ N CH CH CH Et Cl CF₃ OMe N CH CH CH i-Pr Cl CF₃ OMe N CH CH CH t-Bu Cl CF₃ OMe N CH CH CH Et Cl CF₃ CN N CH CH CH i-Pr Cl CF₃ CN N CH CH CH t-Bu Cl CF₃ CN CH N CH N Et Me CF₃ Cl CH N CH N i-Pr Me CF₃ Cl CH N CH N t-Bu Me CF₃ Cl CH N CH N Et Me CF₃ Br CH N CH N i-Pr Me CF₃ Br CH N CH N t-Bu Me CF₃ Br CH N CH N Et Me CF₃ I CH N CH N i-Pr Me CF₃ I CH N CH N t-Bu Me CF₃ I CH N CH N Et Me CF₃ F CH N CH N i-Pr Me CF₃ F CH N CH N t-Bu Me CF₃ F CH N CH N Et Me CF₃ Me CH N CH N i-Pr Me CF₃ Me CH N CH N t-Bu Me CF₃ Me CH N CH N Et Me CF₃ CF₃ CH N CH N i-Pr Me CF₃ CF₃ CH N CH N t-Bu Me CF₃ CF₃ CH N CH N Et Me CF₃ OMe CH N CH N i-Pr Me CF₃ OMe CH N CH N t-Bu Me CF₃ OMe CH N CH N Et Me CF₃ CN CH N CH N i-Pr Me CF₃ CN CH N CH N t-Bu Me CF₃ CN CH N CH N Et Cl CF₃ Cl CH N CH N i-Pr Cl CF₃ Cl CH N CH N t-Bu Cl CF₃ Cl CH N CH N Et Cl CF₃ Br CH N CH N i-Pr Cl CF₃ Br CH N CH N t-Bu Cl CF₃ Br CH N CH N Et Cl CF₃ I CH N CH N i-Pr Cl CF₃ I CH N CH N t-Bu Cl CF₃ I CH N CH N Et Cl CF₃ F CH N CH N i-Pr Cl CF₃ F CH N CH N t-Bu Cl CF₃ F CH N CH N Et Cl CF₃ Me CH N CH N i-Pr Cl CF₃ Me CH N CH N t-Bu Cl CF₃ Me CH N CH N Et Cl CF₃ CF₃ CH N CH N i-Pr Cl CF₃ CF₃ CH N CH N t-Bu Cl CF₃ CF₃ CH N CH N Et Cl CF₃ OMe CH N CH N i-Pr Cl CF₃ OMe CH N CH N t-Bu Cl CF₃ OMe CH N CH N Et Cl CF₃ CN CH N CH N i-Pr Cl CF₃ CN CH N CH N t-Bu Cl CF₃ CN CH CH CH CCl Et Me CF₃ Cl CH CH CH CCl i-Pr Me CF₃ Cl CH CH CH CCl t-Bu Me CF₃ Cl CH CH CH CCl Et Me CF₃ Br CH CH CH CCl i-Pr Me CF₃ Br CH CH CH CCl t-Bu Me CF₃ Br CH CH CH CCl Et Me CF₃ I CH CH CH CCl i-Pr Me CF₃ I CH CH CH CCl t-Bu Me CF₃ I CH CH CH CCl Et Me CF₃ F CH CH CH CCl i-Pr Me CF₃ F CH CH CH CCl t-Bu Me CF₃ F CH CH CH CCl Et Me CF₃ Me CH CH CH CCl i-Pr Me CF₃ Me CH CH CH CCl t-Bu Me CF₃ Me CH CH CH CCl Et Me CF₃ CF₃ CH CH CH CCl i-Pr Me CF₃ CF₃ CH CH CH CCl t-Bu Me CF₃ CF₃ CH CH CH CCl Et Me CF₃ OMe CH CH CH CCl i-Pr Me CF₃ OMe CH CH CH CCl t-Bu Me CF₃ OMe CH CH CH CCl Et Me CF₃ CN CH CH CH CCl i-Pr Me CF₃ CN CH CH CH CCl t-Bu Me CF₃ CN CH CH CH CCl Et Cl CF₃ Cl CH CH CH CCl i-Pr Cl CF₃ Cl CH CH CH CCl t-Bu Cl CF₃ Cl CH CH CH CCl Et Cl CF₃ Br CH CH CH CCl i-Pr Cl CF₃ Br CH CH CH CCl t-Bu Cl CF₃ Br CH CH CH CCl Et Cl CF₃ I CH CH CH CCl i-Pr Cl CF₃ I CH CH CH CCl t-Bu Cl CF₃ I CH CH CH CCl Et Cl CF₃ F CH CH CH CCl i-Pr Cl CF₃ F CH CH CH CCl t-Bu Cl CF₃ F CH CH CH CCl Et Cl CF₃ Me CH CH CH CCl i-Pr Cl CF₃ Me CH CH CH CCl t-Bu Cl CF₃ Me CH CH CH CCl Et Cl CF₃ CF₃ CH CH CH CCl i-Pr Cl CF₃ CF₃ CH CH CH CCl t-Bu Cl CF₃ CF₃ CH CH CH CCl Et Cl CF₃ OMe CH CH CH CCl i-Pr Cl CF₃ OMe CH CH CH CCl t-Bu Cl CF₃ OMe CH CH CH CCl Et Cl CF₃ CN CH CH CH CCl i-Pr Cl CF₃ CN CH CH CH CCl t-Bu Cl CF₃ CN CH CH CH CF Et Me CF₃ Cl CH CH CH CF i-Pr Me CF₃ Cl CH CH CH CF t-Bu Me CF₃ Cl CH CH CH CF Et Me CF₃ Br CH CH CH CF i-Pr Me CF₃ Br CH CH CH CF t-Bu Me CF₃ Br CH CH CH CF Et Me CF₃ I CH CH CH CF i-Pr Me CF₃ I CH CH CH CF t-Bu Me CF₃ I CH CH CH CF Et Me CF₃ F CH CH CH CF i-Pr Me CF₃ F CH CH CH CF t-Bu Me CF₃ F CH CH CH CF Et Me CF₃ Me CH CH CH CF i-Pr Me CF₃ Me CH CH CH CF t-Bu Me CF₃ Me CH CH CH CF Et Me CF₃ CF₃ CH CH CH CF i-Pr Me CF₃ CF₃ CH CH CH CF t-Bu Me CF₃ CF₃ CH CH CH CF Et Me CF₃ OMe CH CH CH CF i-Pr Me CF₃ OMe CH CH CH CF t-Bu Me CF₃ OMe CH CH CH CF Et Me CF₃ CN CH CH CH CF i-Pr Me CF₃ CN CH CH CH CF t-Bu Me CF₃ CN CH CH CH CF Et Cl CF₃ Cl CH CH CH CF i-Pr Cl CF₃ Cl CH CH CH CF t-Bu Cl CF₃ Cl CH CH CH CF Et Cl CF₃ Br CH CH CH CF i-Pr Cl CF₃ Br CH CH CH CF t-Bu Cl CF₃ Br CH CH CH CF Et Cl CF₃ I CH CH CH CF i-Pr Cl CF₃ I CH CH CH CF t-Bu Cl CF₃ I CH CH CH CF i-Pr Cl CF₃ F CH CH CH CF t-Bu Cl CF₃ F CH CH CH CF Et Cl CF₃ Me CH CH CH CF i-Pr Cl CF₃ Me CH CH CH CF t-Bu Cl CF₃ Me CH CH CH CF Et Cl CF₃ CF₃ CH CH CH CF i-Pr Cl CF₃ CF₃ CH CH CH CF t-Bu Cl CF₃ CF₃ CH CH CH CF Et Cl CF₃ OMe CH CH CH CF i-Pr Cl CF₃ OMe CH CH CH CF t-Bu Cl CF₃ OMe CH CH CH CF Et Cl CF₃ CN CH CH CH CF i-Pr Cl CF₃ CN CH CH CH CF t-Bu Cl CF₃ CN CH CH CH CH Et Me C₂F₅ Cl CH CH CH CH i-Pr Me C₂F₅ Cl CH CH CH CH t-Bu Me C₂F₅ Cl CH CH CH CH Et Me C₂F₅ Br CH CH CH CH i-Pr Me C₂F₅ Br CH CH CH CH t-Bu Me C₂F₅ Br CH CH CH CH Et Me C₂F₅ I CH CH CH CH i-Pr Me C₂F₅ I CH CH CH CH t-Bu Me C₂F₅ I CH CH CH CH Et Me C₂F₅ F CH CH CH CH i-Pr Me C₂F₅ F CH CH CH CH t-Bu Me C₂F₅ F CH CH CH CH Et Me C₂F₅ Me CH CH CH CH i-Pr Me C₂F₅ Me CH CH CH CH t-Bu Me C₂F₅ Me CH CH CH CH Et Me C₂F₅ CF₃ CH CH CH CH i-Pr Me C₂F₅ CF₃ CH CH CH CH t-Bu Me C₂F₅ CF₃ CH CH CH CH Et Me C₂F₅ OMe CH CH CH CH i-Pr Me C₂F₅ OMe CH CH CH CH t-Bu Me C₂F₅ OMe CH CH CH CH Et Me C₂F₅ CN CH CH CH CH i-Pr Me C₂F₅ CN CH CH CH CH t-Bu Me C₂F₅ CN CH CH CH CH Et Cl C₂F₅ Cl CH CH CH CH i-Pr Cl C₂F₅ Cl CH CH CH CH t-Bu Cl C₂F₅ Cl CH CH CH CH Et Cl C₂F₅ Br CH CH CH CH i-Pr Cl C₂F₅ Br CH CH CH CH t-Bu Cl C₂F₅ Br CH CH CH CH Et Cl C₂F₅ I CH CH CH CH i-Pr Cl C₂F₅ I CH CH CH CH t-Bu Cl C₂F₅ I CH CH CH CH Et Cl C₂F₅ F CH CH CH CH i-Pr Cl C₂F₅ F CH CH CH CH t-Bu Cl C₂F₅ F CH CH CH CH Et Cl C₂F₅ Me CH CH CH CH i-Pr Cl C₂F₅ Me CH CH CH CH t-Bu Cl C₂F₅ Me CH CH CH CH Et Cl C₂F₅ CF₃ CH CH CH CH i-Pr Cl C₂F₅ CF₃ CH CH CH CH t-Bu Cl C₂F₅ CF₃ CH CH CH CH Et Cl C₂F₅ OMe CH CH CH CH i-Pr Cl C₂F₅ OMe CH CH CH CH t-Bu Cl C₂F₅ OMe CH CH CH CH Et Cl C₂F₅ CN CH CH CH CH i-Pr Cl C₂F₅ CN CH CH CH CH t-Bu Cl C₂F₅ CN

TABLE 17

W X Y Z R³ R⁴ R⁷ R⁸ CH CH CH CH Et Me CF₃ Cl CH CH CH CH i-Pr Me CF₃ Cl CH CH CH CH t-Bu Me CF₃ Cl CH CH CH CH Et Me CF₃ Br CH CH CH CH i-Pr Me CF₃ Br CH CH CH CH t-Bu Me CF₃ Br CH CH CH CH Et Me CF₃ I CH CH CH CH i-Pr Me CF₃ I CH CH CH CH t-Bu Me CF₃ I CH CH CH CH Et Me CF₃ F CH CH CH CH i-Pr Me CF₃ F CH CH CH CH t-Bu Me CF₃ F CH CH CH CH Et Me CF₃ Me CH CH CH CH i-Pr Me CF₃ Me CH CH CH CH t-Bu Me CF₃ Me CH CH CH CH Et Me CF₃ CF₃ CH CH CH CH i-Pr Me CF₃ CF₃ CH CH CH CH t-Bu Me CF₃ CF₃ CH CH CH CH Et Me CF₃ OMe CH CH CH CH i-Pr Me CF₃ OMe CH CH CH CH t-Bu Me CF₃ OMe CH CH CH CH Et Me CF₃ CN CH CH CH CH i-Pr Me CF₃ CN CH CH CH CH t-Bu Me CF₃ CN CH CH CH CH Et Cl CF₃ Cl CH CH CH CH i-Pr Cl CF₃ Cl CH CH CH CH t-Bu Cl CF₃ Cl CH CH CH CH Et Cl CF₃ Br CH CH CH CH i-Pr Cl CF₃ Br CH CH CH CH t-Bu Cl CF₃ Br CH CH CH CH Et Cl CF₃ I CH CH CH CH i-Pr Cl CF₃ I CH CH CH CH t-Bu Cl CF₃ I CH CH CH CH Et Cl CF₃ F CH CH CH CH i-Pr Cl CF₃ F CH CH CH CH t-Bu Cl CF₃ F CH CH CH CH Et Cl CF₃ Me CH CH CH CH i-Pr Cl CF₃ Me CH CH CH CH t-Bu Cl CF₃ Me CH CH CH CH Et Cl CF₃ CF₃ CH CH CH CH i-Pr Cl CF₃ CF₃ CH CH CH CH t-Bu Cl CF₃ CF₃ CH CH CH CH Et Cl CF₃ OMe CH CH CH CH i-Pr Cl CF₃ OMe CH CH CH CH t-Bu Cl CF₃ OMe CH CH CH CH Et Cl CF₃ CN CH CH CH CH i-Pr Cl CF₃ CN CH CH CH CH t-Bu Cl CF₃ CN CH CH CH N Et Me CF₃ Cl CH CH CH N i-Pr Me CF₃ Cl CH CH CH N t-Bu Me CF₃ Cl CH CH CH N Et Me CF₃ Br CH CH CH N i-Pr Me CF₃ Br CH CH CH N t-Bu Me CF₃ Br CH CH CH N Et Me CF₃ I CH CH CH N i-Pr Me CF₃ I CH CH CH N t-Bu Me CF₃ I CH CH CH N Et Me CF₃ F CH CH CH N i-Pr Me CF₃ F CH CH CH N t-Bu Me CF₃ F CH CH CH N Et Me CF₃ Me CH CH CH N i-Pr Me CF₃ Me CH CH CH N t-Bu Me CF₃ Me CH CH CH N Et Me CF₃ CF₃ CH CH CH N i-Pr Me CF₃ CF₃ CH CH CH N t-Bu Me CF₃ CF₃ CH CH CH N Et Me CF₃ OMe CH CH CH N i-Pr Me CF₃ OMe CH CH CH N t-Bu Me CF₃ OMe CH CH CH N Et Me CF₃ CN CH CH CH N i-Pr Me CF₃ CN CH CH CH N t-Bu Me CF₃ CN CH CH CH N Et Cl CF₃ Cl CH CH CH N i-Pr Cl CF₃ Cl CH CH CH N t-Bu Cl CF₃ Cl CH CH CH N Et Cl CF₃ Br CH CH 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CF₃ OMe CH CH N CH t-Bu Me CF₃ OMe CH CH N CH Et Me CF₃ CN CH CH N CH i-Pr Me CF₃ CN CH CH N CH t-Bu Me CF₃ CN CH CH N CH Et Cl CF₃ Cl CH CH N CH i-Pr Cl CF₃ Cl CH CH N CH t-Bu Cl CF₃ Cl CH CH N CH Et Cl CF₃ Br CH CH N CH i-Pr Cl CF₃ Br CH CH N CH t-Bu Cl CF₃ Br CH CH N CH Et Cl CF₃ I CH CH N CH i-Pr Cl CF₃ I CH CH N CH t-Bu Cl CF₃ I CH CH N CH Et Cl CF₃ F CH CH N CH i-Pr Cl CF₃ F CH CH N CH t-Bu Cl CF₃ F CH CH N CH Et Cl CF₃ Me CH CH N CH i-Pr Cl CF₃ Me CH CH N CH t-Bu Cl CF₃ Me CH CH N CH Et Cl CF₃ CF₃ CH CH N CH i-Pr Cl CF₃ CF₃ CH CH N CH t-Bu Cl CF₃ CF₃ CH CH N CH Et Cl CF₃ OMe CH CH N CH i-Pr Cl CF₃ OMe CH CH N CH t-Bu Cl CF₃ OMe CH CH N CH Et Cl CF₃ CN CH CH N CH i-Pr Cl CF₃ CN CH CH N CH t-Bu Cl CF₃ CN CH N CH CH Et Me CF₃ Cl CH N CH CH i-Pr Me CF₃ Cl CH N CH CH t-Bu Me CF₃ Cl CH N CH CH Et Me CF₃ Br CH N CH CH i-Pr Me CF₃ Br CH N CH CH t-Bu Me CF₃ Br CH N CH CH Et Me CF₃ I CH N CH CH i-Pr Me CF₃ I CH N CH CH t-Bu Me CF₃ I CH N CH CH Et Me CF₃ F CH N CH CH i-Pr Me CF₃ F CH N CH CH t-Bu Me CF₃ F CH N CH CH Et Me CF₃ Me CH N CH CH i-Pr Me CF₃ Me CH N CH CH t-Bu Me CF₃ Me CH N CH CH Et Me CF₃ CF₃ CH N CH CH i-Pr Me CF₃ CF₃ CH N CH CH t-Bu Me CF₃ CF₃ CH N CH CH Et Me CF₃ OMe CH N CH CH i-Pr Me CF₃ OMe CH N CH CH t-Bu Me CF₃ OMe CH N CH CH Et Me CF₃ CN CH N CH CH i-Pr Me CF₃ CN CH N CH CH t-Bu Me CF₃ CN CH N CH CH Et Cl CF₃ Cl CH N CH CH i-Pr Cl CF₃ Cl CH N CH CH t-Bu Cl CF₃ Cl CH N CH CH Et Cl CF₃ Br CH N CH CH i-Pr Cl CF₃ Br CH N CH CH t-Bu Cl CF₃ Br CH N CH CH Et Cl CF₃ I CH N CH CH i-Pr Cl CF₃ I CH N CH CH t-Bu Cl CF₃ I CH N CH CH Et Cl CF₃ F CH N CH CH i-Pr Cl CF₃ F CH N CH CH t-Bu Cl CF₃ F CH N CH CH Et Cl CF₃ Me CH N CH CH i-Pr Cl CF₃ Me CH N CH CH t-Bu Cl CF₃ Me CH N CH CH Et Cl CF₃ CF₃ CH N CH CH i-Pr Cl CF₃ CF₃ CH N CH CH t-Bu Cl CF₃ CF₃ CH N CH CH Et Cl CF₃ OMe CH N CH CH i-Pr Cl CF₃ OMe CH N CH CH t-Bu Cl CF₃ OMe CH N CH CH Et Cl CF₃ CN CH N CH CH i-Pr Cl CF₃ CN CH N CH CH t-Bu Cl CF₃ CN N CH CH CH Et Me CF₃ Cl N CH CH CH i-Pr Me CF₃ Cl N CH CH CH t-Bu Me CF₃ Cl N CH CH CH Et Me CF₃ Br N CH CH CH i-Pr Me CF₃ Br N CH CH CH t-Bu Me CF₃ Br N CH CH CH Et Me CF₃ I N CH CH CH i-Pr Me CF₃ I N CH CH CH t-Bu Me CF₃ I N CH CH CH Et Me CF₃ F N CH CH CH i-Pr Me CF₃ F N CH CH CH t-Bu Me CF₃ F N CH CH CH Et Me CF₃ Me N CH CH CH i-Pr Me CF₃ Me N CH CH CH t-Bu Me CF₃ Me N CH CH CH Et Me CF₃ CF₃ N CH CH CH i-Pr Me CF₃ CF₃ N CH CH CH t-Bu Me CF₃ CF₃ N CH CH CH Et Me CF₃ OMe N CH CH CH i-Pr Me CF₃ OMe N CH CH CH t-Bu Me CF₃ OMe N CH CH CH Et Me CF₃ CN N CH CH CH i-Pr Me CF₃ CN N CH CH CH t-Bu Me CF₃ CN N CH CH CH Et Cl CF₃ Cl N CH CH CH i-Pr Cl CF₃ Cl N CH CH CH t-Bu Cl CF₃ Cl N CH CH CH Et Cl CF₃ Br N CH CH CH i-Pr Cl CF₃ Br N CH CH CH t-Bu Cl CF₃ Br N CH CH CH Et Cl CF₃ I N CH CH CH i-Pr Cl CF₃ I N CH CH CH t-Bu Cl CF₃ I N CH CH CH Et Cl CF₃ F N CH CH CH i-Pr Cl CF₃ F N CH CH CH t-Bu Cl CF₃ F N CH CH CH Et Cl CF₃ Me N CH CH CH i-Pr Cl CF₃ Me N CH CH CH t-Bu Cl CF₃ Me N CH CH CH Et Cl CF₃ CF₃ N CH CH CH i-Pr Cl CF₃ CF₃ N CH CH CH t-Bu Cl CF₃ CF₃ N CH CH CH Et Cl CF₃ OMe N CH CH CH i-Pr Cl CF₃ OMe N CH CH CH t-Bu Cl CF₃ OMe N CH CH CH Et Cl CF₃ CN N CH CH CH i-Pr Cl CF₃ CN N CH CH CH t-Bu Cl CF₃ CN CH N CH N Et Me CF₃ Cl CH N CH N i-Pr Me CF₃ Cl CH N CH N t-Bu Me CF₃ Cl CH N CH N Et Me CF₃ Br CH N CH N i-Pr Me CF₃ Br CH N CH N t-Bu Me CF₃ Br CH N CH N Et Me CF₃ I CH N CH N i-Pr Me CF₃ I CH N CH N t-Bu Me CF₃ I CH N CH N Et Me CF₃ F CH N CH N i-Pr Me CF₃ F CH N CH N t-Bu Me CF₃ F CH N CH N Et Me CF₃ Me CH N CH N i-Pr Me CF₃ Me CH N CH N t-Bu Me CF₃ Me CH N CH N Et Me CF₃ CF₃ CH N CH N i-Pr Me CF₃ CF₃ CH N CH N t-Bu Me CF₃ CF₃ CH N CH N Et Me CF₃ OMe CH N CH N i-Pr Me CF₃ OMe CH N CH N t-Bu Me CF₃ OMe CH N CH N Et Me CF₃ CN CH N CH N i-Pr Me CF₃ CN CH N CH N t-Bu Me CF₃ CN CH N CH N Et Cl CF₃ Cl CH N CH N i-Pr Cl CF₃ Cl CH N CH N t-Bu Cl CF₃ Cl CH N CH N Et Cl CF₃ Br CH N CH N i-Pr Cl CF₃ Br CH N CH N t-Bu Cl CF₃ Br CH N CH N Et Cl CF₃ I CH N CH N i-Pr Cl CF₃ I CH N CH N t-Bu Cl CF₃ I CH N CH N Et Cl CF₃ F CH N CH N i-Pr Cl CF₃ F CH N CH N t-Bu Cl CF₃ F CH N CH N Et Cl CF₃ Me CH N CH N i-Pr Cl CF₃ Me CH N CH N t-Bu Cl CF₃ Me CH N CH N Et Cl CF₃ CF₃ CH N CH N i-Pr Cl CF₃ CF₃ CH N CH N t-Bu Cl CF₃ CF₃ CH N CH N Et Cl CF₃ OMe CH N CH N i-Pr Cl CF₃ OMe CH N CH N t-Bu Cl CF₃ OMe CH N CH N Et Cl CF₃ CN CH N CH N i-Pr Cl CF₃ CN CH N CH N t-Bu Cl CF₃ CN CH CH CH CCl Et Me CF₃ Cl CH CH CH CCl i-Pr Me CF₃ Cl CH CH CH CCl t-Bu Me CF₃ Cl CH CH CH CCl Et Me CF₃ Br CH CH CH CCl i-Pr Me CF₃ Br CH CH CH CCl t-Bu Me CF₃ Br CH CH CH CCl Et Me CF₃ I CH CH CH CCl i-Pr Me CF₃ I CH CH CH CCl t-Bu Me CF₃ I CH CH CH CCl Et Me CF₃ F CH CH CH CCl i-Pr Me CF₃ F CH CH CH CCl t-Bu Me CF₃ F CH CH CH CCl Et Me CF₃ Me CH CH CH CCl i-Pr Me CF₃ Me CH CH CH CCl t-Bu Me CF₃ Me CH CH CH CCl Et Me CF₃ CF₃ CH CH CH CCl i-Pr Me CF₃ CF₃ CH CH CH CCl t-Bu Me CF₃ CF₃ CH CH CH CCl Et Me CF₃ OMe CH CH CH CCl i-Pr Me CF₃ OMe CH CH CH CCl t-Bu Me CF₃ OMe CH CH CH CCl Et Me CF₃ CN CH CH CH CCl i-Pr Me CF₃ CN CH CH CH CCl t-Bu Me CF₃ CN CH CH CH CCl Et Cl CF₃ Cl CH CH CH CCl i-Pr Cl CF₃ Cl CH CH CH CCl t-Bu Cl CF₃ Cl CH CH CH CCl Et Cl CF₃ Br CH CH CH CCl i-Pr Cl CF₃ Br CH CH CH CCl t-Bu Cl CF₃ Br CH CH CH CCl Et Cl CF₃ I CH CH CH CCl i-Pr Cl CF₃ I CH CH CH CCl t-Bu Cl CF₃ I CH CH CH CCl Et Cl CF₃ F CH CH CH CCl i-Pr Cl CF₃ F CH CH CH CCl t-Bu Cl CF₃ F CH CH CH CCl Et Cl CF₃ Me CH CH CH CCl i-Pr Cl CF₃ Me CH CH CH CCl t-Bu Cl CF₃ Me CH CH CH CCl Et Cl CF₃ CF₃ CH CH CH CCl i-Pr Cl CF₃ CF₃ CH CH CH CCl t-Bu Cl CF₃ CF₃ CH CH CH CCl Et Cl CF₃ OMe CH CH CH CCl i-Pr Cl CF₃ OMe CH CH CH CCl t-Bu Cl CF₃ OMe CH CH CH CCl Et Cl CF₃ CN CH CH CH CCl i-Pr Cl CF₃ CN CH CH CH CCl t-Bu Cl CF₃ CN CH CH CH CF Et Me CF₃ Cl CH CH CH CF i-Pr Me CF₃ Cl CH CH CH CF t-Bu Me CF₃ Cl CH CH CH CF Et Me CF₃ Br CH CH CH CF i-Pr Me CF₃ Br CH CH CH CF t-Bu Me CF₃ Br CH CH CH CF Et Me CF₃ I CH CH CH CF i-Pr Me CF₃ I CH CH CH CF t-Bu Me CF₃ I CH CH CH CF Et Me CF₃ F CH CH CH CF i-Pr Me CF₃ F CH CH CH CF t-Bu Me CF₃ F CH CH CH CF Et Me CF₃ Me CH CH CH CF i-Pr Me CF₃ Me CH CH CH CF t-Bu Me CF₃ Me CH CH CH CF Et Me CF₃ CF₃ CH CH CH CF i-Pr Me CF₃ CF₃ CH CH CH CF t-Bu Me CF₃ CF₃ CH CH CH CF Et Me CF₃ OMe CH CH CH CF i-Pr Me CF₃ OMe CH CH CH CF t-Bu Me CF₃ OMe CH CH CH CF Et Me CF₃ CN CH CH CH CF i-Pr Me CF₃ CN CH CH CH CF t-Bu Me CF₃ CN CH CH CH CF Et Cl CF₃ Cl CH CH CH CF i-Pr Cl CF₃ Cl CH CH CH CF t-Bu Cl CF₃ Cl CH CH CH CF Et Cl CF₃ Br CH CH CH CF i-Pr Cl CF₃ Br CH CH CH CF t-Bu Cl CF₃ Br CH CH CH CF Et Cl CF₃ I CH CH CH CF i-Pr Cl CF₃ I CH CH CH CF t-Bu Cl CF₃ I CH CH CH CF i-Pr Cl CF₃ F CH CH CH CF t-Bu Cl CF₃ F CH CH CH CF Et Cl CF₃ Me CH CH CH CF i-Pr Cl CF₃ Me CH CH CH CF t-Bu Cl CF₃ Me CH CH CH CF Et Cl CF₃ CF₃ CH CH CH CF i-Pr Cl CF₃ CF₃ CH CH CH CF t-Bu Cl CF₃ CF₃ CH CH CH CF Et Cl CF₃ OMe CH CH CH CF i-Pr Cl CF₃ OMe CH CH CH CF t-Bu Cl CF₃ OMe CH CH CH CF Et Cl CF₃ CN CH CH CH CF i-Pr Cl CF₃ CN CH CH CH CF t-Bu Cl CF₃ CN CH CH CH CH Et Me C₂F₅ Cl CH CH CH CH i-Pr Me C₂F₅ Cl CH CH CH CH t-Bu Me C₂F₅ Cl CH CH CH CH Et Me C₂F₅ Br CH CH CH CH i-Pr Me C₂F₅ Br CH CH CH CH t-Bu Me C₂F₅ Br CH CH CH CH Et Me C₂F₅ I CH CH CH CH i-Pr Me C₂F₅ I CH CH CH CH t-Bu Me C₂F₅ I CH CH CH CH Et Me C₂F₅ F CH CH CH CH i-Pr Me C₂F₅ F CH CH CH CH t-Bu Me C₂F₅ F CH CH CH CH Et Me C₂F₅ Me CH CH CH CH i-Pr Me C₂F₅ Me CH CH CH CH t-Bu Me C₂F₅ Me CH CH CH CH Et Me C₂F₅ CF₃ CH CH CH CH i-Pr Me C₂F₅ CF₃ CH CH CH CH t-Bu Me C₂F₅ CF₃ CH CH CH CH Et Me C₂F₅ OMe CH CH CH CH i-Pr Me C₂F₅ OMe CH CH CH CH t-Bu Me C₂F₅ OMe CH CH CH CH Et Me C₂F₅ CN CH CH CH CH i-Pr Me C₂F₅ CN CH CH CH CH t-Bu Me C₂F₅ CN CH CH CH CH Et Cl C₂F₅ Cl CH CH CH CH i-Pr Cl C₂F₅ Cl CH CH CH CH t-Bu Cl C₂F₅ Cl CH CH CH CH Et Cl C₂F₅ Br CH CH CH CH i-Pr Cl C₂F₅ Br CH CH CH CH t-Bu Cl C₂F₅ Br CH CH CH CH Et Cl C₂F₅ I CH CH CH CH i-Pr Cl C₂F₅ I CH CH CH CH t-Bu Cl C₂F₅ I CH CH CH CH Et Cl C₂F₅ F CH CH CH CH i-Pr Cl C₂F₅ F CH CH CH CH t-Bu Cl C₂F₅ F CH CH CH CH Et Cl C₂F₅ Me CH CH CH CH i-Pr Cl C₂F₅ Me CH CH CH CH t-Bu Cl C₂F₅ Me CH CH CH CH Et Cl C₂F₅ CF₃ CH CH CH CH i-Pr Cl C₂F₅ CF₃ CH CH CH CH t-Bu Cl C₂F₅ CF₃ CH CH CH CH Et Cl C₂F₅ OMe CH CH CH CH i-Pr Cl C₂F₅ OMe CH CH CH CH t-Bu Cl C₂F₅ OMe CH CH CH CH Et Cl C₂F₅ CN CH CH CH CH i-Pr Cl C₂F₅ CN CH CH CH CH t-Bu Cl C₂F₅ CN

Formulation/Utility

Compounds of this invention will generally be used as a formulation or composition with an agriculturally suitable carrier comprising at least one of a liquid diluent, a solid diluent or a surfactant. The formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature. Useful formulations include liquids such as solutions (including emulsifiable concentrates), suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like which optionally can be thickened into gels. Useful formulations further include solids such as dusts, powders, granules, pellets, tablets, films, and the like which can be water-dispersible (“wettable”) or water-soluble. Active ingredient can be (micro)encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or “overcoated”). Encapsulation can control or delay release of the active ingredient. Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High-strength compositions are primarily used as intermediates for further formulation.

The formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges that add up to 100 percent by weight.

Weight Percent Active Ingredient Diluent Surfactant Water-Dispersible and Water-  5-90  0-94 1-15 soluble Granules, Tablets and Powders. Suspensions, Emulsions,  5-50 40-95 0-15 Solutions (including Emulsifiable Concentrates) Dusts  1-25 70-99 0-5  Granules and Pellets 0.01-99      5-99.99 0-15 High Strength Compositions 90-99  0-10 0-2 

Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, N.J. Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, N.J., as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth and the like, or thickeners to increase viscosity.

Surfactants include, for example, polyethoxylated alcohols, polyethoxylated alkylphenols, polyethoxylated sorbitan fatty acid esters, dialkyl sulfosuccinates, alkyl sulfates, alkylbenzene sulfonates, organosilicones, N,N-dialkyltaurates, lignin sulfonates, naphthalene sulfonate formaldehyde condensates, polycarboxylates, and polyoxyethylene/polyoxypropylene block copolymers. Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, starch, sugar, silica, talc, diatomaceous earth, urea, calcium carbonate, sodium carbonate and bicarbonate, and sodium sulfate. Liquid diluents include, for example, water, N,N-dimethylformamide, dimethyl sulfoxide, N-alkylpyrrolidone, ethylene glycol, polypropylene glycol, paraffins, alkylbenzenes, alkylnaphthalenes, oils of olive, castor, linseed, tung, sesame, corn, peanut, cotton-seed, soybean, rape-seed and coconut, fatty acid esters, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-methyl-2-pentanone, and alcohols such as methanol, cyclohexanol, decanol and tetrahydrofurfuryl alcohol.

Solutions, including emulsifiable concentrates, can be prepared by simply mixing the ingredients. Dusts and powders can be prepared by blending and, usually, grinding as in a hammer mill or fluid-energy mill. Suspensions are usually prepared by wet-milling; see, for example, U.S. Pat. No. 3,060,084. Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, “Agglomeration”, Chemical Engineering, Dec. 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546. Pellets can be prepared as described in U.S. Pat. No. 4,172,714. Water-dispersible and water-soluble granules can be prepared as taught in U.S. Pat. Nos. 4,144,050, 3,920,442 and DE 3,246,493. Tablets can be prepared as taught in U.S. Pat. Nos. 5,180,587, 5,232,701 and 5,208,030. Films can be prepared as taught in GB 2,095,558 and U.S. Pat. No. 3,299,566.

For further information regarding the art of formulation, see U.S. Pat. No. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41; U.S. Pat. No. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S. Pat. No. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81-96; and Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989.

In the following Examples, all percentages are by weight and all formulations are prepared in conventional ways. Compound numbers refer to compounds in Index Tables A.

EXAMPLE A Wettable Powder Compound 1 65.0% dodecylphenol polyethylene glycol ether  2.0% sodium ligninsulfonate  4.0% sodium silicoaluminate  6.0% montmorillonite (calcined)  23.0%.

EXAMPLE B Granule Compound 1 10.0% attapulgite granules (low volatile matter,  90.0%. 0.71/0.30 mm; U.S.S. No. 25-50 sieves)

EXAMPLE C Extruded Pellet Compound 1 25.0% anhydrous sodium sulfate 10.0% crude calcium ligninsulfonate  5.0% sodium alkylnaphthalenesulfonate  1.0% calcium/magnesium bentonite  59.0%.

EXAMPLE D Emulsifiable Concentrate Compound 1 20.0% blend of oil soluble sulfonates and polyoxyethylene ethers 10.0% isophorone  70.0%.

The compounds of this invention exhibit activity against a wide spectrum of foliar-feeding, fruit-feeding, stem or root feeding, seed-feeding, aquatic and soil-inhabiting arthropods (term “arthropods” includes insects, mites and nematodes) which are pests of growing and stored agronomic crops, forestry, greenhouse crops, ornamentals, nursery crops, stored food and fiber products, livestock, household, and public and animal health. Those skilled in the art will appreciate that not all compounds are equally effective against all growth stages of all pests. Nevertheless, all of the compounds of this invention display activity against pests that include: eggs, larvae and adults of the Order Lepidoptera; eggs, foliar-feeding, fruit-feeding, root-feeding, seed-feeding larvae and adults of the Order Coleoptera; eggs, immatures and adults of the Orders Hemiptera and Homoptera; eggs, larvae, nymphs and adults of the Order Acari; eggs, immatures and adults of the Orders Thysanoptera, Orthoptera and Dermaptera; eggs, immatures and adults of the Order Diptera; and eggs, juveniles and adults of the Phylum Nematoda. The compounds of this invention are also active against pests of the Orders Hymenoptera, Isoptera, Siphonaptera, Blattaria, Thysanura and Psocoptera; pests belonging to the Class Arachnida and Phylum Platyhelminthes. Specifically, the compounds are active against southern corn rootworm (Diabrotica undecimpunctata howardi), aster leafhopper (Mascrosteles fascifrons), boll weevil (Anthonomus grandis), two-spotted spider mite (Tetranychus urticae), fall armyworm (Spodoptera frugiperda), black bean aphid (Aphis fabae), green peach aphid (Myzus persica), cotton aphid (Aphis gossypii), Russian wheat aphid (Diuraphis noxia), English grain aphid (Sitobion avenae), whitefly (Bemisia tabacii), tobacco budworm (Heliothis virescens), rice water weevil (Lissorhoptrus oryzophilus), rice leaf beetle (Oulema oryzae), whitebacked planthopper (Sogatella furcifera), green leafhopper (Nephotettix cincticeps), brown planthopper (Nilaparvata lugens), small brown planthopper (Laodelphax striatellus), rice stem borer (Chilo suppressalis), rice leafroller (Cnaphalocrocis medinalis), black rice stink bug (Scotinophara lurida), rice stink bug (Oebalus pugnax), rice bug (Leptocorisa chinensis), slender rice bug (Cletus puntiger), southern green stink bug (Nezara viridula) and german cockroach (Blatella germanica). The compounds are active on mites, demonstrating ovicidal, larvicidal and chemosterilant activity against such families as Tetranychidae including Tetranychus urticae, Tetranychus cinnabarinus, Tetranychus mcdanieli, Tetranychus pacificus, Tetranychus turkestani, Byrobia rubrioculus, Panonychus ulmi, Panonychus citri, Eotetranychus carpini borealis, Eotetranychus, hicoriae, Eotetranychus sexmaculatus, Eotetranychus yumensis, Eotetranychus banksi and Oligonychus pratensis; Tenuipalpidae including Brevipalpus lewisi, Brevipalpus phoenicis, Brevipalpus californicus and Brevipalpus obovatus; Eriophyidae including Phyllocoptruta oleivora, Eriophyes sheldoni, Aculus cornutus, Epitrimerus pyri and Eriophyes mangiferae. See WO 90/10623 and WO 92/00673 for more detailed pest descriptions.

Compounds of this invention can also be mixed with one or more other insecticides, fungicides, nematocides, bactericides, acaricides, growth regulators, chemosterilants, semiochemicals, repellents, attractants, pheromones, feeding stimulants or other biologically active compounds to form a multi-component pesticide giving an even broader spectrum of agricultural protection. Examples of such agricultural protectants with which compounds of this invention can be formulated are: insecticides such as abamectin, acephate, avermectin, azinphos-methyl, bifenthrin, buprofezin, carbofuran, chlorfenapyr, chlorpyrifos, chlorpyrifos-methyl, clothianidin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, cypermethrin, deltamethrin, diafenthiuron, diazinon, diflubenzuron, dimethoate, diofenolan, emamectin, endosulfan, esfenvalerate, fenothicarb, fenoxycarb, fenpropathrin, fenvalerate, fipronil, flucythrinate, tau-fluvalinate, flufenoxuron, fonophos, imidacloprid, isofenphos, malathion, metaldehyde, methamidophos, methidathion, methomyl, methoprene, methoxychlor, methyl 7-chloro-2,5-dihydro-2-[[N-(methoxycarbonyl)-N-[4-(trifluoromethoxy)phenyl]amino]carbonyl]indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylate (indoxacarb), monocrotophos, oxamyl, parathion, parathion-methyl, permethrin, phorate, phosalone, phosmet, phosphamidon, pirimicarb, profenofos, pymetrozine, pyriproxyphen, rotenone, spionsad, sulprofos, tebufenozide, tefluthrin, terbufos, tetrachlorvinphos, thiacloprid, thiodicarb, tralomethrin, trichlorfon and triflumuron; fungicides such as acibenzolar, azoxystrobin, benomyl blasticidin-S, Bordeaux mixture (Tribasic copper sulfate), bromuconazole, carpropamid (KTU 3616), captafol, captan, carbendazim, chloroneb, chlorothalonil, copper oxychloride, copper salts, cymoxanil, cyproconazole, cyprodinil (CGA 219417),(S)-3,5-dichloro-N-(3-chloro-1-ethyl-1-methyl-2-oxopropyl)-4-methylbenzamide (RH 7281), diclocymet (S-2900), diclomezine, dicloran, difenoconazole,(S)-3,5-dihydro-5-methyl-2-(methylthio)-5-phenyl-3-(phenylamino)-4H-imidazol-4-one (RP 407213), dimethomorph, diniconazole, diniconazole-M, dodine, edifenphos, epoxiconazole (BAS 480F), famoxadone, fenamidone, fenarimol, fenbuconazole, fencaramid (SZX0722), fenpiclonil fenpropidin, fenpropimorph, fentin acetate, fentin hydroxide, fluazinam, fludioxonil, flumetover (RPA 403397), fluquinconazole, flusilazole, flutolanil, flutriafol, folpet, fosetyl-aluminum, furalaxyl, furametapyr (S-82658), hexaconazole, ipconazole, iprobenfos, iprodione, isoprothiolane, kasugamycin, kresoxim-methyl, mancozeb, maneb, mefenoxam, mepronil, metalaxyl, metconazole, metominostrobin/fenominostrobin (SSF-126), myclobutanil, neo-asozin (ferric methanearsonate), oxadixyl, penconazole, pencycuron, probenazole, prochloraz, propamocarb, propiconazole, pyrifenox, pyraclostrobin, pyrimethanil, pyroquilon, quinoxyfen, spiroxamine, sulfur, tebuconazole, tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, triadimefon, triadimenol, tricyclazole, trifloxystrobin, triticonazole, validamycin and vinclozolin; nematocides such as aldicarb, oxamyl and fenamiphos; bactericides such as streptomycin; acaricides such as amitraz, chinomethionat, chlorobenzilate, cyhexatin, dicofol, dienochlor, etoxazole, fenazaquin, fenbutatin oxide, fenpropathrin, fenpyroximate, hexythiazox, propargite, pyridaben and tebufenpyrad; and biological agents such as Bacillus thuringiensis, Bacillus thuringiensis delta endotoxin, baculovirus, and entomopathogenic bacteria, virus and fungi.

Preferred insecticides and acaricides for mixing with compounds of this invention include pyrethroids such as cypermethrin, cyhalothrin, cyfluthin and beta-cyfluthrin, esfenvalerate, fenvalerate and tralomethrin; carbamates such as fenothicarb, methomyl, oxamyl and thiodicarb; neonicotinoids such as clothianidin, imidacloprid and thiacloprid, neuronal sodium channel blockers such as indoxacarb, insecticidal macrocyclic lactones such as spinosad, abamectin, avermectin and emamectin; GABA antagonists such as endosulfan and fipronil; insecticidal ureas such as flufenoxuron and triflumuron, juvenile hormone mimics such as diofenolan and pyriproxyphen; pymetrozine; and amitraz Preferred biological agents for mixing with compounds of this invention include Bacillus thuringiensis and Bacillus thuringiensis delta endotoxin.

Most preferred mixtures include a mixture of a compound of this invention with cyhalothrin; a mixture of a compound of this invention with beta-cyfluthrin; a mixture of a compound of this invention with esfenvalerate; a mixture of a compound of this invention with methomyl; a mixture of a compound of this invention with imidacloprid; a mixture of a compound of this invention with thiacloprid; a mixture of a compound of this invention with indoxacarb; a mixture of a compound of this invention with abamectin; a mixture of a compound of this invention with endosulfan; a mixture of a compound of this invention with fipronil; a mixture of a compound of this invention with flufenoxuron; a mixture of a compound of this invention with pyriproxyphen; a mixture of a compound of this invention with; a mixture of a compound of this invention with pymetrozine; a mixture of a compound of this invention with amitraz; a mixture of a compound of this invention with Bacillus thuringiensis and a mixture of a compound of this invention with Bacillus thuringiensis delta endotoxin.

In certain instances, combinations with other arthropodicides having a similar spectrum of control but a different mode of action will be particularly advantageous for resistance management.

Arthropod pests are controlled and protection of agronomic, horticultural and specialty crops, animal and human health is achieved by applying one or more of the compounds of this invention, in an effective amount, to the environment of the pests including the agronomic and/or nonagronomic locus of infestation, to the area to be protected, or directly on the pests to be controlled. Thus, the present invention further comprises a method for the control of foliar and soil inhabiting arthropods and nematode pests and protection of agronomic and/or nonagronomic crops, comprising applying one or more of the compounds of the invention, or compositions containing at least one such compound, in an effective amount, to the environment of the pests including the agronomic and/or nonagronomic locus of infestation, to the area to be protected, or directly on the pests to be controlled. A preferred method of application is by spraying. Alternatively, granular formulations of these compounds can be applied to the plant foliage or the soil. Other methods of application include direct and residual sprays, aerial sprays, seed coats, microencapsulations, systemic uptake, baits, eartags, boluses, foggers, fumigants, aerosols, dusts and many others. The compounds can be incorporated into baits that are consumed by the arthropods or in devices such as traps and the like.

The compounds of this invention can be applied in their pure state, but most often application will be of a formulation comprising one or more compounds with suitable carriers, diluents, and surfactants and possibly in combination with a food depending on the contemplated end use. A preferred method of application involves spraying a water dispersion or refined oil solution of the compounds. Combinations with spray oils, spray oil concentrations, spreader stickers, adjuvants, other solvents, and synergists such as piperonyl butoxide often enhance compound efficacy.

The rate of application required for effective control will depend on such factors as the species of arthropod to be controlled, the pest's life cycle, life stage, its size, location, time of year, host crop or animal, feeding behavior, mating behavior, ambient moisture, temperature, and the like. Under normal circumstances, application rates of about 0.01 to 2 kg of active ingredient per hectare are sufficient to control pests in agronomic ecosystems, but as little as 0.001 kg/hectare may be sufficient or as much as 8 kg/hectare may be required. For nonagronomic applications, effective use rates will range from about 1.0 to 50 mg/square meter but as little as 0.1 mg/square meter may be sufficient or as much as 150 mg/square meter may be required.

The following TEST demonstrates the control efficacy of compounds of this invention on specific pests. “Control efficacy” represents inhibition of arthropod development (including mortality) that causes significantly reduced feeding. The pest control protection afforded by the compounds is not limited, however, to these species. See Index Tables A through Q for compound descriptions. The following abbreviations are used in the Index Tables which follow: t is tertiary, n is normal, i is iso, c is cyclo, s is secondary, Me is methyl, Et is ethyl, Pr is propyl, i-Pr is isopropyl, c-Pr is cyclopropyl, Bu is butyl, s-Bu is secondary butyl, Pent is pentyl, OMe is methoxy, OEt is ethoxy, SMe is methylthio, SEt is ethylthio, CN is cyano, NO₂ is nitro, and Het is heterocycle. The abbreviation “Ex.” stands for “Example” and is followed by a number indicating in which example the compound is prepared.

TABLE A INDEX

Compound R¹ R² R³ R⁴ R⁵ and/or R⁶ m.p. ° C. 1 (Ex. 1) H i-Pr H 2-Me 4-OCF₃ 207-209 2 H i-Pr H 5-Cl 2-CF₃ 195-196 3 H i-Pr H 5-Cl 2-Me-4-CF₃ 182-184 4 H i-Pr H 2-Me 4-CF₃ 238-240 5 H i-Pr H 2-Me 4-CO₂Me 216-217 6 H i-Pr H 2-Me 3-NO₂ 230-233 7 H i-Pr H 2-Me 3-CF₃-4-F 223-225 8 H i-Pr H 2-Me 3-CN 237-239 9 H i-Pr H 2-Me 2-OCF₃ 191-193 10 H t-Bu H 2-Me 4-OCF₃ 163-167 11 H t-Bu H 2-Me 4-CO₂Me 164-169 12 H i-Pr H 2-Cl 4-CO₂Me 224-225 13 H t-Bu H 2-Me 2-OCF₃ 203-204 14 H t-Bu H 2-Me 3-NO₂ 193-195 15 H t-Bu H 2-Me 3-CF₃-4-F 198-199 16 H i-Pr H 2-Me 4-OCF₃ 178-181 17 H i-Pr H 2-Me 2-OCF₃ 170-172 18 H i-Pr H 2-OMe 3-CF₃-4-F 209-211 19 H i-Pr H 2-Cl 4-OCF₃ 215-216 20 H i-Pr Me 2-Me 2-OCF₃ 153-155 21 H i-Pr H 5-Me 4-OCF₃ 173-175 22 H i-Pr H 5-Me 2-OCF₃ 180-185 23 H i-Pr H 5-Me 4-CO₂Me 182-184 24 H i-Pr Me 2-Me 4-OCF₃ Glass 25 H i-Pr Me 2-Me 4-CO₂Me 67-73 26 H (1,2-di-Me)-Pr H 2-Me 4-OCF₃ 189-191 27 H CH(CH₃)CH₂OCH₃ H 2-Me 4-OCF₃ 147-148 28 H CH₂CH₂OCH₃ H 2-Me 4-OCF₃ 153-155 29 H 2-Pent H 2-Me 4-OCF₃ 165-168 30 H s-Bu H 2-Me 4-OCF₃ 181-183 31 H propargyl H 2-Me 4-OCF₃ 190-192 32 H n-Pr H 2-Me 4-OCF₃ 189-191 33 H allyl H 2-Me 4-OCF₃ 185-187 34 H Me₂NCH₂CH₂ H 2-Me 4-OCF₃ 168-170 35 H propargyl H 2-Me 4-OCF₃ 202-204 36 H i-Bu H 2-Me 4-OCF₃ 182-183 37 H i-Pr H 2,4-di-Me 4-OCF₃ 205-208 38 H i-Pr H 2,4-di-Me 4-CF₃ >230 39 H i-Pr H 2,4-di-Me 2-OCF₃ 231-232 40 H i-Pr H 2,4-di-Me 4-CO₂Me 219-221 41 H i-Pr H 2,4-di-Me 3-CF₃-4-F 222-224 42 H t-Bu H 2-OMe 4-CF₃ 210-214 43 H t-Bu H 2-OMe 4-OCF₃ 170-173 44 H i-Pr Me 2-Me 3-NO₂ Oil 45 H i-Pr H 2-Cl 4-OCF₃ 187-194 46 H t-Bu H 2-Cl 4-OCF₃ 205-207 47 H allyl H 2-Cl 4-OCF₃ 188-189 48 H s-Bu H 2-Cl 4-OCF₃ 192-193 49 H —CH₂CH₂CH₂CH₂— 2-Me 4-OCF₃ 138-142 50 H CH₂CF₃ H 2-Me 4-OCF₃ >230 51 H c-Bu H 2-Me 4-OCF₃ 218-220 52 (Ex. 3) H i-Pr H 2-Me 2-Me-4-CF₃ 247-248 53 H i-Pr H 5-Me 2-Me-4-CF₃ 186-188 54 H i-Pr H H 4-OCF₃ 185-187 55 H i-Pr H H 3-NO₂ 199-200 56 H i-Pr H H 2-OCF₃ 118-122 57 Me i-Pr H H 4-OCF₃ 117-118 58 Me i-Pr H H 3-NO₂ 134-136 59 Me i-Pr H H 2-OCF₃ 128-130 60 H i-Pr H H 3-CF₃ 176-177 61 H i-Pr H H 2-Me-4-CF₃ 100-106 62 H Me H 2-Me 4-OCF₃ 204-206 63 H Et H 2-Me 4-OCF₃ 198-200 64 H NHi-Pr H 2-Me 4-OCF₃ 126-128 65 H i-Pr H 2-Me 3-CF₃ 198-200 66 H i-Pr H 2-Me 4-CN >230 67 H i-Pr H 2-Me 2-NO₂ >230 68 H i-Pr H 2-Me 3,5-di-CF₃ >230 69 H i-Pr H 2-Me 4-NO₂ 227-230 70 H i-Pr H 2-Me 2-CF₃ 227-230 71 H i-Pr H H 2-Me-4-OCF₃ 118-124 72 H i-Pr H H 4-CF₃ 196-198 73 H i-Pr H 2-Me 2-Me-4-SCF₂H 212-213 74 H t-Bu H 2-Me 2-Me-4-SCF₂H 193-195 75 H i-Pr H 2-Me 2-Me-4-OCF₃ 221-222 76 H t-Bu H 2-Me 4-CF₃ 217-219 77 H t-Bu H 2-Me 3-CF₃ 197-198 78 H t-Bu H 2-Me 3,5-di-CF₃ 206-207 79 H t-Bu H 2-Me 4-CN >230 80 H t-Bu H 2-Me 4-NO₂ >230 81 Me i-Pr H 2-Me 2-CF₃ oil 82 Me i-Pr H 2-Me 4-OCF₃ 151-157 83 Me i-Pr H H 2-Me-4-OCF₃ 103-107 84 Me t-Bu H 2-Me 2-Me-4-CF₃ 233-234 85 H t-Bu H 2-Me 2-Me-4-OCF₃ 207-209 86 H t-Bu H 2-Me 2,5-di-CF₃ 199-201 87 H i-Pr H 2-CF3 4-OCF₃ 183-185 88 H i-Pr H 2-CF3 4-CF₃ 211-212 89 H t-Bu H 2-CF₃ 4-CF₃ 191-192 90 H R-(−)-s-Bu H 2-Me 4-OCF₃ 170-172 91 H S-(+)-s-Bu H 2-Me 4-OCF₃ 177-179 92 Me i-Pr H H 4-CF₃ oil 93 Me i-Pr H 2-OCF₂H 4-OCF₃ 162-164 94 H t-Bu H 2-CF₃ 4-OCF₃ 145-148 95 H i-Pr Me 2-CF₃ 4-CF₃ 151-154 96 H i-Pr Me 2-CF₃ 4-OCF₃ 140-144 97 H i-Pr H 2-OCF₂H 4-CF₃ 224-227 98 H i-Pr H 2,4-di-Me 2-Me-4-CF₃ >230 99 H i-Pr H 2-Cl 2-Me-4-CF₃ >230 100 H CH(CH₃)CH₂OCH₃ H 2-Cl 2-Me-4-CF₃ 194-197 101 H s-Bu H 2-Cl 2-Me-4-CF₃ 212-214 102 H c-Pr H 2-Me 4-OCF₃ 208-210 103 H CH(CH₃)CH₂OCH₃ H 2,4-di-Me 4-OCF₃ 166-168 104 H CH(CH₃)CH₂OCH₃ H 2,4-di-Me 4-CF₃ 192-194 105 H i-Pr H 4-Me 4-CF₃ 212-213 106 H i-Pr H 4-Me 4-OCF₃ 204-205 107 H i-Pr H 2-Br-4-Me 4-OCF₃ >230 108 H t-Bu H 2-Br-4-Me 4-OCF₃ 118-120 109 H i-Pr H 2-NO₂ 4-CF₃ 203-204 110 H t-Bu H 2-NO₂ 4-CF₃ 199-200 111 H i-Pr H 2-NO₂ 4-OCF₃ 204-205 112 H t-Bu H 2-NO₂ 4-OCF₃ 181-183 113 H i-Pr H 2-Me 2-Me-4-S(O)₂CF₂H 218-221 114 H i-Pr H 2-Me 2-Me-4-S(O)CF₂H 203-206 115 H CH(CH₃)CH₂OCH₃ H 3-Cl 4-CF₃ 158-161 116 H i-Pr H 4-Br 4-CF₃ 232-234 117 H t-Bu H 4-Br 4-CF₃ 204-206 118 H CH(CH₃)CH₂OCH₃ H 4-Br 4-CF₃ 157-158 119 H i-Pr H 4-Br 4-OCF₃ 221-222 120 H t-Bu H 4-Br 4-OCF₃ 173-175 121 H CH(CH₃)CH₂OCH₃ H 4-Br 4-OCF₃ 153-155 122 H CH(CH₃)CH₂OCH₃ H 3-Cl 4-OCF₃ 137-140 123 H i-Pr H 4-F 4-CF₃ 205-206 124 H t-Bu H 2-Cl 2-Me-4-CF₃ 237-240 125 H 2-Pent H 2-Me 4-CF₃ 194-196 126 H s-Bu H 2-Me 4-CF₃ 207-210 127 H Et H 2-Me 4-CF₃ >240 128 H Me H 2-Me 4-CF₃ 236-237 129 H i-Pr H 4-F 4-OCF₃ 208-209 130 H CH(CH₃)CH₂OCH₃ H 4-F 4-OCF₃ 151-152 131 H CH(CH₃)CH₂OCH₃ H 2-Me 4-CF₃ 188-190 132 CH₂CO₂Me i-Pr H H 4-CF₃ oil 133 CH₂CO₂Me i-Pr H H 4-OCF₃ oil 134 Me Et H 2-Me 4-CF₃ oil 135 Me Et H 2-Me 4-OCF₃ oil 136 Me Et H 2-Me 2-Me-4-SCF₂H 132-136 137 H CH(CH₃)CH₂OCH₃ H 2-Me-4-Br 4-CF₃ 197-199 138 H CH(CH₃)CH₂OCH₃ H 2-Me-4-Br 4-OCF₃ 188-190 139 H i-Pr H 3-Cl 4-CF₃ 201-202 140 H t-Bu H 3-Cl 4-CF₃ 159-161 141 H i-Pr H 3-Cl 4-OCF₃ 190-192 142 H t-Bu H 3-Cl 4-OCF₃ 150-152 143 H i-Pr H 2-Br-4-Me 4-CF₃ >230 144 H t-Bu H 2-Br-4-Me 4-CF₃ 213-215 145 H CH(CH₃)CH₂OCH₃ H 5-F 4-CF₃ 145-147 146 H

H 2-Me 4-CF₃ >230 147 H i-Pr H 2-Me 2-F-4-CF₃ 224-226 148 H i-Pr H 2-Me 2-CF₃-4-F 223-225 149 H t-Bu H 4-F 4-OCF₃ 180-187 150 H CH(CH₃)CH₂OCH₃ H 2-Me 2-Me-4-CF₃ 194-197 151 H Me H 2-Me 2-Me-4-CF₃ >230 152 H Et H 2-Me 2-Me-4-CF₃ 243-245 153 H

H 2-Me 2-Me-4-CF₃ >230 154 H i-Pr H 3-NO₂ 4-CF₃ 244-246 155 H i-Pr H 3-NO₂ 4-OCF₃ 239-240 156 H t-Bu H 3-NO₂ 4-OCF₃ 180-184 157 H CH(CH₃)CH₂OCH₃ H 3-NO₂ 4-OCF₃ 172-175 158 H t-Bu H 3-NO₂ 4-CF₃ 194-196 159 H CH(CH₃)CH₂OCH₃ H 3-NO₂ 4-CF₃ 178-179 160 H i-Pr H 2-Cl 4-CF₃ >230 161 H CH(CH₃)CH₂OCH₃ H 2-Cl 4-CF₃ 182-185 162 H t-Bu H 5-Cl 2-Me-4-CF₃ 203-205 163 H CH(CH₃)CH₂OCH₃ H 5-Cl 2-Me-4-CF₃ 154-155 164 H i-Pr H 2-Me 2,4-(CF₃)₂ >230 165 H i-Pr H 2-Me 3,4-OCF₂O— 199-200 166 H CH₂CN H 2-Me 4-CF₃ 218-223 167 H CH(CH₃)Ph H 2-Me 4-CF₃ 225-228 168 H CH(CH₃)Ph H 2-Me 4-OCF₃ 208-210 169 H t-Bu H 2-Cl 4-CF₃ 191-193 170 H i-Pr Me 2-Cl 4-CF₃ 136-140 171 H i-Pr H 2-Me 4-SO₂CH₃ >250 172 H i-Pr H 5-Cl 4-CF₃ 217-218 173 H t-Bu H 5-Cl 4-CF₃ 231-235 174 H CH(CH₃)CH₂OCH₃ H S-Cl 4-CF₃ 175-177 175 H i-Pr H 4-I 4-CF₃ >230 176 H t-Bu H 4-I 4-CF₃ 215-219 177 H CH(CH₃)CH₂OCH₃ H 4-I 4-CF₃ 173-178 178 H i-Pr H 4-I 4-OCF₃ >230 179 H t-Bu H 4-I 4-OCF₃ 192-194 180 H CH(CH₃)CH₂OCH₃ H 4-I 4-OCF₃ 178-180 181 H CH₂(3-pyridinyl) H 2-Me 4-CF₃ 198-199 182 H CH₂CN H 2-Me 2-Me-4-CF₃ >230 183 H CH(CH₃)CO₂CH₃ H 2-Me 4-CF₃ 223-225 184 H i-Pr H 2-F 4-CF₃ 228-229 185 H i-Pr H 5-F 4-CF₃ 169-170 186 H i-Pr H 2-F 2-Me-4-OCF₃ 206-208 187 H i-Pr H 5-F 2-Me-4-OCF₃ 125-126 188 H i-Pr H 2-F 2-Me-4-CF₃ 234-235 189 H i-Pr H 5-F 2-Me-4-CF₃ 133-135 190 H CH₂(3-pyridinyl) H 2-Me 4-OCF₃ 201-202 191 H CH₂CH₂SCH₃ H 2-Me 4-CF₃ 187-188 192 H CH₂CH₂SCH₃ H 2-Me 2-Me-4-CF₃ 250-251 193 H CH₂CH₂SEt H 2-Me 4-CF₃ 190-191 194 H CH₂CH₂SEt H 2-Me 2-Me-4-CF₃ 228-230 195 H CH(CH₃)CH═CH₂ H 2-Me 2-Me-4-CF₃ 211-214 196 H i-Pr H 2-Et 4-CF₃ 228-230 197 H CH(CH₃)CH₂OCH₃ H 2-Et 4-CF₃ 176-177 198 H i-Pr H 2-Me 3,4-OCF₂CF₂O— 218-220 199 H i-Pr H 2-Me 2-(CONMe₂)-4,5-Cl₂ 229-230 200 H i-Pr H 2-Me 2-(CO-1-piperidinyl)-4,5-Cl₂ 202-205 201 H t-Bu H 2-Et 4-CF₃ 187-191 202 H CH(CH₃)CH₂SCH₃ H 2-Et 2-Me-4-CF₃ 206-208 203 H i-Pr H 2-Me 2-(CONMe₂)-4-Br 191-194 204 H i-Pr H 2-Me 2-(CONMe₂)-5-Br 190-194 205 H CH(CH₃)CH₂SO₂CH₃ H 2-Me 2-Me-4-CF₃ 231-233 206 H c-Pr H 2-Me 2-Me-4-CF₃ 258-261 207 H c-Pr H 2-Cl 2-Me-4-CF₃ >260 208 H i-Pr H 2-I 2-Me-4-OCF₃ 241-242 209 H i-Pr H 2-I 2-Me-4-CF₃ 260-262 210 H i-Pr H 2-Me 2-(CONMe₂)-4-F 164-170 211 H i-Pr H 2-Me 2-(CONMe₂)-5-F 167-171 212 H i-Pr H 2-Me 2-(CO-1-piperidiyl)-4-Br 105-117 213 H CH(CH₃)CH₂OH H 2-Me 2-Me-4-CF₃ 179-180 214 H CH(CH₃)CH₂OH H 2-Cl 2-Me-4-CF₃ 183-185 215 H i-Pr H 2-Cl 2-(CONMe₂)-4-Br 165-170 216 H i-Pr H 2-Cl 2-(CONMe₂)-5-Br 179-181 217 H i-Pr H 2-Me 2-(3-CF₃-1-pyrazolyl)-4-CF₃ 243-244 218 H i-Pr H 2-Me 2-(1-(1,2,4-triazolyl))-4-CF₃ 238-240 219 H i-Pr H 2-Me 2-(3-Br-1-pyrazolyl)-4-CF₃ >250 220 H i-Pr H 2-Me 2-(3-CN-1-pyrazolyl)-4-CF₃ >250 221 H i-Pr H 2-Me 2-(4-CF₃-1-imidazolyl)-4-CF₃ >250 222 H i-Pr H 2-Me 2-(3-CH₃-1-pyrazolyl)-4-CF₃ 248-250 223 H i-Pr H 2-Me 2-(2-CH₃-1-imidazolyl)-4-CF₃ 186-188 224 H i-Pr H 2-Me 2-(3-CF3-1-(1,2,4-triazolyl))-4-CF₃ 254-256 225 H i-Pr H 2-Me 2-(1-pyrazolyl)-4-CF₃ 246-248 226 H i-Pr H 2-Me 2-(3-CO₂Et-5-Me-1-pyrazolyl)-4-CF₃ 224-225 227 H i-Pr H 2-Me 2-(1-imidazolyl)-4-CF₃ 240-241 228 H i-Pr H 2-Me 2-(3-CF₃-5-Me-1-pyrazolyl)-4-CF₃ 229-231 229 H i-Pr H 2-Me 2-(3,5-Me₂-1-pyrazolyl)-4-CF₃ 214-218 230 H i-Pr H 2-Me 2-(2,4-Me₂-1-imidazolyl)-4-CF₃ 246-248 231 H i-Pr H 2-Me 2-(4-Me-1-imidazolyl)-4-CF₃ 223-225 232 H i-Pr H 2-Cl 2-(3-CF₃-1-pyrazolyl)-4-CF₃ >250 233 H i-Pr H 2-Cl 2-(1-(1,2,4-triazolyl))-4-CF₃ 252-254 234 H i-Pr H 2-Cl 2-(3-Br-1-pyrazolyl)-4-CF₃ >250 235 H i-Pr H 2-Cl 2-(3-CO₂Et-5-Me-1-pyrazolyl)-4-CF₃ 220-221 236 H i-Pr H 2-Cl 2-(4-CO₂Me-1-imidazolyl)-4-CF₃ 255-257 237 H i-Pr H 2-Cl 2-(3-CN-1-pyrazolyl)-4-CF₃ >250 238 H i-Pr H 2-Cl 2-(1-imidazolyl)-4-CF₃ 248-249 239 H i-Pr H 2-Me 2-(4-CO₂Me-1-imidazolyl)-4-CF₃ 219-222 240 H i-Pr H 2-Me 2-(2-thienyl)-4-CF₃ 241-243 241 H i-Pr H 2-Me 2-(3-thienyl)-4-CF₃ 229-231 242 H i-Pr H 2-Me 2-(2-furanyl)-4-CF₃ 246-247 243 H i-Pr H 2-Me 2-(3-t-Bu-1-pyrazolyl)-4-CF₃ 247-249 244 H i-Pr H 2-Me 2-(3-s-Bu-1-pyrazolyl)-4-CF₃ 224-225 245 H i-Pr H 2-Me 2-(3-c-Pr-1-pyrazolyl)-4-CF₃ 220-221 246 H i-Pr H 2-Me 2-(3-Me-5-isoxazolyl)-4-CF₃ 233-234 247 H i-Pr H 2-Me

>250 248 H i-Pr H 2-Me 2-(CONMe₂)-4-CF₃ 188-192 249 H i-Pr H 2-Me 2-(CONMe₂)-5-CF₃ 194-196 250 H i-Pr H 2-Me 2-(CO-1-pyrrolidinyl)-4-CF₃ 201-204 251 H i-Pr H 2-Me 2-(CO-1-pyrrolidinyl)-5-CF₃ 221-223 252 H i-Pr H 2-Me 2-OCH₃-4-CF₃ 188-189 253 H i-Pr H 2-Me 2-(3-Cl-5-isoxazolyl)-4-CF₃ 247-248 254 H i-Pr H 2-Me 2-Oi-Pr-4-CF₃ 158-159 255 H i-Pr H 2-Cl 2-(4-Me-1-pyrazolyl)-4-CF₃ 252-253 256 H i-Pr H 2-Me 2-(4-Me-1-pyrazolyl)-4-CF₃ 226-227 257 H i-Pr H 2,5-Cl₂ 2-Me-4-CF₃ 235-237 258 H i-Pr H 2-Me 4-Ph 221-224 259 H i-Pr H 2-Me 4-(4-OCH₃)Ph >230 260 H i-Pr H 2-Me 4-(2-Me)Ph 156-158 261 H i-Pr H 2-Me 4-(3-CH₃)Ph 225-226 262 H i-Pr H 2-Me 4-(3-CF₃)Ph 214-215 263 H i-Pr H 2-Me 4-(4-F)Ph >230 264 H —CH₂CH₂CH₂CH₂— 2-Cl 3-Cl 158-161 265 H

H 2-Me 4-OCF₃ >230 266 H i-Pr H 2-CF₃ 2-Me-4-Br >230 267 H t-Bu H 2-CF₃ 2-Me-4-Br 234-236 268 H i-Pr Me 2-CF₃ 2-Me-4-Br 154-158 269 H CH(CH₃)CH₂OCH₃ H 2-CF₃ 2-Me-4-Br 202-204 270 H s-Bu H 2-CF₃ 2-Me-4-Br >230 271 H s-pentyl H 2-CF₃ 2-Me-4-Br 215-217 272 H i-Pr H 2-CH₃ 2-Me-4-CF₃ >230 273 H i-Pr Me 2-OCHF₂ 2-Me-4-Br 224-227 274 H i-Pr H 2-CH₃ 2-(CONMe₂)-4-CF₃ 130-137 275 B is S H i-Pr H 2-Me 2-Me-4-CF₃ 193-195 276 H i-Pr H 2-Cl 2-(1-pyrazolyl)-4-CF₃ 249-250 277 B is S H i-Pr H 2-Me 4-OCF₃ 169-171 278 B is S H i-Pr H 2-Me 4-CF₃Ph 204-206

TABLE B INDEX

Compound R² R³ (R⁴)_(n) R⁷(a) R⁷(b) m.p. ° C. B1 (Ex. 4) i-Pr H 2-Me CF₃ CH₃ 247-248 B2 i-Pr H 2-Me OCH₂CF₃ H 188-191 B3 i-Pr H 2-Cl CF₃ CH₃ 234-236 B4 t-Bu H 2-Cl CF₃ CH₃ 243-245 B4 CH(CH₃)CH₂OCH₃ H 2-Cl CF₃ CH₃ 198-201 B6 CH(CH₃)CH═CH₂ H 2-Me CF₃ CH₃ 226-227 B7 i-Pr H 2-Cl OCH₂CF₃ H 208-210 B8 t-Bu H 2-Cl OCH₂CF₃ H 174-175 B9 CH(CH₃)CH₂OCH₃ H 2-Cl OCH₂CF₃ H 163-165 B10 i-Pr H 2-Me CF₃ H 208-211 B11 CH(CH₃)CH₂OCH₃ H 2-Me CF₃ CH₃ 187-191 B12 s-Bu H 2-Me CF₃ CH₃ 215-218 B13 2-pentyl H 2-Me CF₃ CH₃ 213-215 B14 i-Pr H 2-Me Cl H 235-237 B15 i-Pr H 2-Me H Cl 235-237 B16 i-Pr H 2-OCHF₂ CF₃ CH₃ 221-224 B17 i-Pr H 2-Me CF₂CF₃ CH₃ 208-209 B18 t-Bu H 2-Me CF₂CF₃ CH₃ 211-212 B19 CH(CH₃)CH₂OCH₃ H 2-Me CF₂CF₃ CH₃ 193-196 B20 t-Bu H 2-CF₃ CF₃ CH₃ >250 B21 t-Bu H 2-CF₃ CF₃ CH₃ 218-222 B22 CH(CH₃)CH₂OCH₃ H 2-CF₃ CF₃ CH₃ 200-202 B23 i-Pr H 2-Me CF₃ Br 253-255 B24 CH(CH₃)CH₂SCH₃ H 2-Me CF₃ CH₃ 222-223 B25 CH(CH₃)CH₂CN H 2-Me CF₃ CH₃ 230-232 B26 CH₂CH₂CN H 2-Me CF₃ CH₃ >260 B27 c-Pr H 2-Me CF₃ CH₃ >260 B28 i-Pr H 2-Me CF₃ OCH₃ 181-183 B29 i-Pr H 2-Me Cl CH₃ 246-247 B30 i-Pr H 2-Me CF₃ Ph >250 B31 i-Pr H 2-I CF₃ CH₃ 256-257 B32 i-Pr H 2-F CF₃ CH₃ 218-220 B33 i-Pr H 5-F CF₃ CH₃ 144-146 B34 CH(CH₃)CH₂SO₂CH₃ H 2-Me CF₃ CH₃ 243-245 B35 CH(CH₃)CH₂OH H 2-Me CF₃ CH₃ 222-223 B36 CH(CH₃)CH₂COCH₃ H 2-Me CF₃ CH₃ 204-206 B37 i-Pr H 2-Me CF₃ CH₂OCH₃ 241-242 B38 i-Pr H 2-Me CF₃ CH₂CH₃ 229-231 B39 i-Pr H 2-Me CH₃ Cl 236-237 B40 i-Pr H 2-Me CH₃ 2-pyridinyl 278-281 B41 t-Bu H 2-Me CF₃ CH₃ 234-236 B42 i-Pr H 2-Me CF₃ n-Pr 224-226 B43 i-Pr Me 2-Me CF₃ CH₃ 202-205 B44 i-Pr H 2-Me c-Pr CH₃ 226-229 B45 i-Pr H 2-Me c-Pr CH₃, HCl salt >230 B46 i-Pr H 2-Me CF₃ Cl 248-254 B47 i-Pr H 2-Me CF₃ i-Pr 235-237 B48 i-Pr H 2-Me CF₃ 1-(1,2,4-triazolyl) >260 B49 i-Pr H 2-Br CF₃ CH₃ 247-248 B50 i-Pr H 2-Me OCH₂CF₃ CH₃ 150-160 B51 i-Pr H 2-Me CF₃ 2-phenoxy 231-232 B52 i-Pr H 2-Me CF₃ 1-morpholinyl >250 B53 i-Pr H 2-Me CF₃ 1-(3-CF₃-imidazolyl) 247-250 B54 i-Pr H 2-Me CF₃ 1-(3-Br-pyrazolyl) >260 B55 i-Pr H 2-Me CF₃ 1-(3-CF₃-pyrazolyl) >260 B56 i-Pr H 2-Me CF₃ 1-((3-CF₃)-1,2,4-triazolyl) >260 B57 i-Pr H 2-Me CF₃ 1-((3-CN)-1,2,4-triazolyl) >260 B58 i-Pr H 2-Me i-Bu Cl 185-190 B59 i-Pr H 2-Me CF₃ 2-MePh 200-203 B60 i-Pr H 2-Me i-Pr CH₃ 186-190 B61 i-Pr H 2-Me Ph Cl 229-234 B62 i-Pr H 2-Me CF₃ SCH₂CH(CH₃)2 230-231 B63 i-Pr H 2-Me CF₂CF₃ CH₂CH₃ 209-211 B64 i-Pr H 2-Me CF₃ 1-pyrazolyl >250 B65 i-Pr H 2-Me CF₂CF₃ H >250 B66 i-Pr H 2-Me CF₂CF₃ i-Pr 209-212 B67 i-Pr H 2-Me, 4-Br CF₃ CH₃ >250 B68 i-Pr H 2-Me OCH₂CF₃ n-Pr 165-169 B69 i-Pr H 2-Me Cl n-Pr 200-205 B70 i-Pr H 2-Me Cl Et 200-205 B71 i-Pr H 2-Me CF₃ CN 214-215 B72 i-Pr H 2,5-Cl₂ CF₃ CH₃ >240 B73 i-Pr H 2-Me H H, R⁷(c) is SPh 223-225 B74 B is S, i-Pr H 2-Me CF₃ CH₃ 201-203 B75 B is S, i-Pr H 2-Me CF₃ Et 173-175 B76 B is S, i-Pr H 2-Me CF₂CF₃ CH₃ 156-158 B77 i-Pr H 2-Me H 1-((3-CF₃)-pyrazolyl) 224-225 B78 i-Pr H 2-Me CF₃ 2-ClPh 223-225

TABLE C INDEX

Compound R² R³ (R⁴)_(n) R⁷(a) R⁷(b) m.p. ° C. C1 (Ex. 5) i-Pr H 2-Me CF₃ CH₃ 252-253 C2 i-Pr H 2-Cl CF₃ CH₃ 260-262 C3 i-Pr H 2-Me CF₃ OCH₃ 195-196 C4 i-Pr H 2-Me CF₃ N(CH₃)₂ 270-272 C5 i-Pr H 2-Me CF₃ Et 246-248 C6 i-Pr H 2-Me CF₃ Ph 175-177 C7 i-Pr H 2-Me i-Pr Et 179-182 C8 i-Pr H 2-Me c-Pr Et 202-204 C9 i-Pr H 2-Me i-Pr CH₃ 206-209 C10 i-Pr H 2-Me c-Pr CH₃ 222-225 C11 i-Pr H 2-Me c-Pr Ph 236-239 C12 i-Pr H 2-Me CF₃ SCH₃ 244-247 C13 i-Pr H 2-Me CF₃ 1-pyrrolidinyl 272-273 C14 i-Pr H 2-Me CF₃ OCH₂C(Cl)═CH₂ 142-144 C15 Et H 2-Me CF₃ 2-MePh 253-256 C16 i-Pr H 2-Me CF₃ 2-MePh 244-246 C17 t-Bu H 2-Me CF₃ 2-MePh 251-253 C18 Et H 2-Cl CF₃ 2-MePh 242-243 C19 i-Pr H 2-Cl CF₃ 2-MePh 237-240 C20 t-Bu H 2-Cl CF₃ 2-MePh 253-255 C21 Et H 2-Me CF₃ 2-ClPh 251-252 C22 i-Pr H 2-Me CF₃ 2-ClPh 246-248 C23 t-Bu H 2-Me CF₃ 2-ClPh 238-239 C24 Et H 2-Cl CF₃ 2-ClPh 248-249 C25 i-Pr H 2-Cl CF₃ 2-ClPh 254-255 C26 t-Bu H 2-Cl CF₃ 2-ClPh 240-242 C27 Et H 2-Me CF₃ c-Pr 236-238 C28 i-Pr H 2-Me CF₃ c-Pr 240-241 C29 t-Bu H 2-Me CF₃ c-Pr 246-248 C30 Et H 2-Cl CF₃ c-Pr 240-242 C31 i-Pr H 2-Cl CF₃ c-Pr 232-235 C32 t-Bu H 2-Cl CF₃ c-Pr 266-268 C33 Et H 2-Me CF₃ i-Pr 230-231 C34 i-Pr H 2-Me CF₃ i-Pr 211-214 C35 t-Bu H 2-Me CF₃ i-Pr 210-213 C36 Et H 2-Cl CF₃ i-Pr 247-249 C37 i-Pr H 2-Cl CF₃ i-Pr 236-239 C38 t-Bu H 2-Cl CF₃ i-Pr 235-238 C39 Et H 2-Me CF₂CF₃ 2-MePh 247 C40 i-Pr H 2-Me CF₂CF₃ 2-MePh 218-220 C41 t-Bu H 2-Me CF₂CF₃ 2-MePh 224-226 C42 Et H 2-Cl CF₂CF₃ 2-MePh 241-243 C43 i-Pr H 2-Cl CF₂CF₃ 2-MePh 232-234 C44 t-Bu H 2-Cl CF₂CF₃ 2-MePh 237-239 C45 Et H 2-Me CF₂CF₃ 2-ClPh 255-257 C46 i-Pr H 2-Me CF₂CF₃ 2-ClPh 224 C47 t-Bu H 2-Me CF₂CF₃ 2-ClPh 215 C48 Et H 2-Cl CF₂CF₃ 2-ClPh 248-250 C49 i-Pr H 2-Cl CF₂CF₃ 2-ClPh 222-224 C50 t-Bu H 2-Cl CF₂CF₃ 2-ClPh 242 C51 Et H 2-Me CF₂CF₃ Ph 246-248 C52 i-Pr H 2-Me CF₂CF₃ Ph 220 C53 t-Bu H 2-Me CF₂CF₃ Ph 242 C54 Et H 2-Cl CF₂CF₃ Ph 238-240 C55 i-Pr H 2-Cl CF₂CF₃ Ph 260 C56 t-Bu H 2-Cl CF₂CF₃ Ph 231-232 C57 i-Pr H 2-Me CF₂CF₃ CH₃ 208 C58 t-Bu H 2-Me CF₂CF₃ CH₃ 242-244 C59 Et H 2-Cl CF₂CF₃ CH₃ 210-212 C60 i-Pr H 2-Cl CF₂CF₃ CH₃ 195 C61 t-Bu H 2-Cl CF₂CF₃ CH₃ 246-248 C62 Et H 2-Me CF₂CF₃ c-Pr 224-225 C63 i-Pr H 2-Me CF₂CF₃ c-Pr 232-234 C64 Et H 2-Cl CF₂CF₃ c-Pr 216-218 C65 i-Pr H 2-Cl CF₂CF₃ c-Pr 218-220 C66 t-Bu H 2-Cl CF₂CF₃ c-Pr 210-212 C67 Et H 2-Me CF₂CF₃ i-Pr 218-220 C68 i-Pr H 2-Me CF₂CF₃ i-Pr 196-198 C69 t-Bu H 2-Me CF₂CF₃ i-Pr 212-214 C70 Et H 2-Cl CF₂CF₃ i-Pr 216-220 C71 i-Pr H 2-Cl CF₂CF₃ i-Pr 215-218 C72 t-Bu H 2-Cl CF₂CF₃ i-Pr 240-244 C73 i-Pr H 2-Me CF₂CF₃ Et 210-212 C74 Et H 2-Me CF₂CF₃ Et 230-232 C75 Et H 2-Cl CF₂CF₃ Et 210-213 C76 i-Pr H 2-Cl CF₂CF₃ Et 203-204 C77 t-Bu H 2-Cl CF₂CF₃ Et 230-232 C78 Et H 2-Me CF₂CF₃ CH₃ 238-240 C79 Bis S i-Pr H 2-Me CF₃ Et 190-193 C80 i-Pr H 2-Me CF₃ 2-CF₃Ph 255-258

TABLE D INDEX

Compound R² R³ (R⁴)_(n) R⁷(a) R⁷(b) m.p. ° C. D1 i-Pr H 2-Me CF₃ CH₃ 200-204 D2 (Ex. 2) i-Pr H 2-Me CF₃ Et 123-126 D3 i-Pr H 2-Cl CF₃ CH₃ 233-235 D4 t-Bu H 2-Me CF₃ Et 215-218 D5 i-Pr H 2-Me CH₃ Ph 238-239 D6 i-Pr H 2-Me CH₃ CH₃ 206-208 D7 i-Pr H 2-Me CH₃ CH₂CF₃ 246-248 D8 i-Pr H 2-Cl Et CF₃ 235-237 D9 i-Pr H 2-Me CH₃ CH₃, R⁷ (c) is Cl 205-207 D10 i-Pr H 2-Me CH₃ 4-CF₃Ph 256-258 D11 i-Pr H 2-Me CH₃ 2-CF₃Ph 204-206 D12 t-Bu H 2-Me CH₃ Ph 236-238 D13 i-Pr H 2-F CH₃ Ph 227-229 D14 i-Pr H 5-F CH₃ Ph 209-211 D15 i-Pr H 2-Cl CH₃ Ph 233-234 D16 i-Pr H H CH₃ Ph 215-217 D17 i-Pr H 2-NO₂ CH₃ Ph 236-237 D18 i-Pr H 2-Cl CF₃ Ph 240-242 D19 (Ex. 6) i-Pr H 2-Me CF₃ Ph 260-262 D20 i-Pr H 2-I CH₃ Ph 250-251 D21 i-Pr H 2-I CH₃ 2-CF₃Ph 251-253 D22 H H 2-Me CH₃ Ph 253-255 D23 Et Et 2-Me CH₃ Ph 182-184 D24 t-Bu H 2-Cl CF₃ Ph 232-234 D25 i-Pr H 2-I CF₃ Ph 271-273 D26 t-Bu H 2-I CF₃ Ph 249-250 D27 i-Pr H 2-Me CH₃ t-Bu 210-211 D28 i-Pr H 2-Br CF₃ Ph 257-259 D29 i-Pr H 2-Br CH₃ Ph 246-247 D30 i-Pr H 2-Me CF₃ 2-pyridinyl 237-238 D31 i-Pr H 2,5-Cl₂ CF₃ Ph >250 D32 B is S, i-Pr H 2-Me CF₃ Ph 169-172 D33 i-Pr H 2-Me CF₃ 2-ClPh 208-209 D34 i-Pr H 2-Cl CF₃ 2-ClPh 234-235 D35 i-Pr H 2-Me CF₃ 4-ClPh 289-290 D36 i-Pr H 2-Cl CF₃ 4-ClPh 276-278 D37 i-Pr H 2-Cl CF₃ 2-pyridinyl 239-240 D38 i-Pr H 2-Me CF₃ 2-pyrimidinyl 205-208 D39 i-Pr H 2-Me CF₃ 2-(3-CH₃-pyridinyl) 183-187 D40 i-Pr H 2-Me CF₂CF₃ Ph 231-232 D41 i-Pr H 2-Cl CF₂CF₃ Ph 206-207 D42 t-Bu H 2-Cl CF₂CF₃ Ph 212-213 D43 i-Pr H 2-Br CF₂CF₃ Ph 219-222 D44 i-Pr H 2-Me CF₃ 3-ClPh 278-280 D45 i-Pr H 2-Cl CF₃ 3-ClPh 272-273 D46 i-Pr H 2-Me CF₃ 2-FPh 217-218 D47 i-Pr H 2-Cl CF₃ 2-FPh 220-221 D48 i-Pr H 2-Me CF₃ 4-FPh 269-270 D49 i-Pr H 2-Cl CF₃ 4-FPh 279-280 D50 i-Pr H 2-I c-Pr CH₃ 222-224 D51 i-Pr H 5-I c-Pr CH₃ 215-217 D52 i-Pr H 2-CF₃ CF₃ Ph 247-249 D53 i-Pr H 2-Cl CF₃ i-Pr 255-258 D54 i-Pr H 2-Me CF₃ 3-FPh 277-278 D55 i-Pr H 2-Cl CF₃ 3-FPh 256-257 D56 i-Pr H 2-Me CF₃ 2-CF₃Ph 215-216 D57 i-Pr H 2-Cl CF₃ 2-CF₃Ph 230-231 D58 i-Pr H 2-Me CF₃ 2-BrPh 207-208 D59 i-Pr H 2-Cl CF₃ 2-BrPh 239-240 D60 i-Pr H 2-OCH₃ CF₃ Ph 215-216 D61 i-Pr H 5-Cl CF₃ 2-(3-CH₃-pyridinyl) 224-225 D62 i-Pr H 2-Me CF₃ 2-(3-Cl-pyridinyl) 179-181 D63 s-Bu H 2-Cl CF₃ Ph >240 D64 c-Pr H 2-Cl CF₃ Ph >240 D65 Et H 2-Cl CF₃ Ph >240 D66 t-Bu H 2-CF₃ CF₃ Ph 230-233 D67 Et H 2-CF₃ CF₃ Ph 246-249 D68 CH(CH₃)CH₂SCH₃ H 2-CF₃ CF₃ Ph 215-217 D69 CH(CH₃)CH₂OCH₃ H 2-CF₃ CF₃ Ph 220-223 D70 i-Pr H 5-Cl CF₃ 2-(3-Cl-pyridinyl) 230-233 D71 i-Pr H 5-Me CF₃ 2-thiazolyl 201-203 D72 i-Pr H 5-Me CF₃ 2-pyrazinyl 252-253 D73 i-Pr H 5-Me CF₃ 4-pyridinyl 224-228 D74 i-Pr H 2-Me CF₃ i-Pr 236-243 D75 i-Pr H 2-Me CF₃ 2-CH₃Ph 211-212 D76 i-Pr H 2-Cl CF₃ 2-CH₃Ph 232-234 D77 i-Pr H 2-Br CF₃ 2-ClPh 247-248 D78 t-Bu H 2-Me CF₃ 2-ClPh 216-217 D79 (Ex. 7) i-Pr H 2-Me CF₃ 2-(3-CF₃-pyridinyl) 227-230 D80 CH₂CH₂Cl H 2-Cl CF₃ Ph 237-242 D81 CH₂CH₂CH₂Cl H 2-Cl CF₃ Ph 233-239 D82 CH(CH₃)CO₂CH₃ H 2-Cl CF₃ Ph 221-222 D83 S-CH(i-Pr)CO₂CH₃ H 2-Cl CF₃ Ph 212-213 D84 i-Pr H 2-Me CF₃ 2,6-Cl₂—Ph 267-268 D85 i-Pr H 2-Cl CF₃ 2,6-Cl₂—Ph 286-287 D86 i-Pr H 2-Me Br Ph 253-255 D87 i-Pr H 2-Cl Br Ph 247-248 D88 i-Pr H 2-Me CF₃ i-Bu 205-210 D89 i-Pr H 2-Me CF₃ CH₂Ph 235-237 D90 i-Pr H 2-Me CF₃ 2-(3-OCH₃-pyridinyl) 221-222 D91 i-Pr H 2-Me CF₃ 3-pyridinyl 260-261 D92 i-Pr H 2-Me CF₃ 4-quinolinyl >260 D93 i-Pr H 2-Me CN 2-(3-Cl-pyridinyl) 203-204 D94 i-Pr H 2-Me CF₃ 2,4-F₂—Ph 245-246 D95 i-Pr H 2-Cl CF₃ 2,4-F₂—Ph 252-253 D96 i-Pr H 2-Me CF₃ 2-Et-Ph 207-209 D97 i-Pr H 2-Cl CF₃ 2-Et-Ph 221-222 D98 i-Pr H H CF₃ 2-ClPh 206-207 D99 t-Bu H H CF₃ 2-ClPh 197-198 D100 CH(CH₃)CH₂OCH₃ H H CF₃ 2-ClPh 145-148 D101 CH(CH₃)CH₂SCH₃ H H CF₃ 2-ClPh 158-160 D102 CH(CH₃)CH₂SCH₃ H 2-Cl CF₃ Ph 184-186 D103 CH(CH₃)CH₂OCH₃ H 2-Cl CF₃ Ph 217-218 D104 n-Pr H 2-Cl CF₃ Ph 247-248 D105 i-Bu H 2-Cl CF₃ Ph 244-245 D106 CH₃ H 2-Cl CF₃ Ph >250 D107 i-Pr Me 2-Cl CF₃ Ph 193-194 D108 CH₂C≡CH H 2-Cl CF₃ Ph >250 D109 CH₂CH═CH₂ H 2-Cl CF₃ Ph 248-249 D110 CH₂(2-furanyl) H 2-Cl CF₃ Ph 246-247 D111 i-Pr H 2-Me Ph 2-ClPh 133-136 D112 i-Pr H 2-Cl Ph 2-ClPh 220-221 D113 i-Pr H 2-Me CF₃ 4-(3,5-Cl₂-pyridinyl) 239-242 D114 i-Pr H 2-Cl CF₃ 4-(3,5-Cl₂-pyridinyl) 229-231 D115 CH(CH₃)CH₂SCH₃ H 2-Me CF₃ 2-ClPh 194-195 D116 CH(CH₃)CH₂OCH₃ H 2-Me CF₃ 2-ClPh 181-183 D117 s-Bu H 2-Me CF₃ 2-ClPh 199-200 D118 c-Pr H 2-Me CF₃ 2-ClPh 234-235 D119 n-Pr H 2-Me CF₃ 2-ClPh 222-223 D120 i-Bu H 2-Me CF₃ 2-ClPh 235-237 D121 Me H 2-Me CF₃ 2-ClPh 242-243 D122 i-Pr Me 2-Me CF₃ 2-ClPh 90-93 D123 CH₂C≡CH H 2-Me CF₃ 2-ClPh 215-216 D124 Et H 2-Me CF₃ 2-ClPh 228-229 D125 CH₂CH═CH₂ H 2-Me CF₃ 2-ClPh 227-228 D126 CH₂(2-furanyl) H 2-Me CF₃ 2-ClPh 218-219 D127 CH(CH₃)CH₂SCH₃ H 2-Me CF₃ Ph 179-180 D128 CH(CH₃)CH₂OCH₃ H 2-Me CF₃ Ph 219-220 D129 s-Bu H 2-Me CF₃ Ph 244-245 D130 c-Pr H 2-Me CF₃ Ph >250 D131 n-Pr H 2-Me CF₃ Ph 238-239 D132 i-Bu H 2-Me CF₃ Ph 237-238 D133 Me H 2-Me CF₃ Ph 263-265 D134 i-Pr Me 2-Me CF₃ Ph 178-179 D135 CH₂C≡CH H 2-Me CF₃ Ph 253-254 D136 Et H 2-Me CF₃ Ph 244-245 D137 CH₂CH═CH₂ H 2-Me CF₃ Ph 240-241 D138 CH₂(2-furanyl) H 2-Me CF₃ Ph 245-246 D139 i-Pr H 2-OCHF₂ CF₃ 2-ClPh 200-201 D140 i-Pr H 2-OCH₃ CF₃ 2-ClPh 206-207 D141 i-Pr H 2-I CF₃ 2-ClPh 253-256 D142 i-Pr H 2-Me Br 2-ClPh 147-150 D143 i-Pr H 2-Cl Br 2-ClPh 246-247 D144 i-Pr H 2-Me CF₃ 2-OCH₃Ph 218-219 D145 i-Pr H 2-Cl CF₃ 2-OCH₃Ph 243-244 D146 i-Pr H 2-Me CF₃ 1-isoquinolinyl 252-253 D147 CH(CH₃)CH₂SCH₃ H 2-Cl CF₃ 2-ClPh 217-218 D148 CH(CH₃)CH₂OCH₃ H 2-Cl CF₃ 2-ClPh 207-208 D149 s-Bu H 2-Cl CF₃ 2-ClPh 216-217 D150 c-Pr H 2-Cl CF₃ 2-ClPh 261-262 D151 n-Pr H 2-Cl CF₃ 2-ClPh 231-232 D152 i-Bu H 2-Cl CF₃ 2-ClPh 255-256 D153 Me H 2-Cl CF₃ 2-ClPh 233-235 D154 i-Pr Me 2-Cl CF₃ 2-ClPh 127-128 D155 CH₂C≡CH H 2-Cl CF₃ 2-ClPh 226-227 D156 Et H 2-Cl CF₃ 2-ClPh 244-246 D157 CH₂CH═CH₂ H 2-Cl CF₃ 2-ClPh 235-236 D158 CH₂(2-furanyl) H 2-Cl CF₃ 2-ClPh 207-208 D159 i-Pr H C≡CSi(CH₃)₃ CF₃ 2-ClPh 256-258 D160 i-Pr H C≡CH CF₃ 2-ClPh 228-230 D161 i-Pr H 2-Cl C≡CH 2-ClPh 219-222 D162 i-Pr H 2-Me H H, R⁷(c) is CH₃ 220-223 D163 i-Pr H 2-Me CH₃ Ph, R⁷(c) is Cl 209-210 D164 B is S i-Pr H 2-Cl CF₃ Ph 169-174 D165 i-Pr H 2-Me CF₃ 2,6-F₂Ph 223-225 D166 i-Pr H 2-Me CF₃ 2-Cl-6-FPh 203-206 D167 i-Pr H 2-Cl CF₃ 2-Cl-6-FPh 218-221 D168 i-Pr H 2-Me-4-Br CF₃ 2-FPh 232-233 D169 t-Bu H 2-Cl CF₃ 2-(3-Cl-pyridinyl) 250-251 D170

H 2-Cl CF₃ 2-(3-Cl-pyridinyl) >250 D171 Et Et 2-Cl CF₃ 2-ClPh 243-247 D172 Me Me 2-Cl CF₃ 2-ClPh 234-235 D173 Et Et 2-Me CF₃ 2-ClPh 237-238 D174 Me Me 2-Me CF₃ 2-ClPh 225-226 D175 CH₂CH₂N(Me)₂ H 2-Me CF₃ 2-ClPh 188-190 D176 i-Pr H 2-Cl CF₃ 2-pyrazinyl 242-243 D177 t-Bu H 2-Me-4-Br CF₃ 2-ClPh >260 D178 CH(CH₃)CH₂OCH₃ H 2-Me CF₃ 2-(3-Cl-pyridinyl) 176-177 D179 CH(CH₃)CH₂SCH₃ H 2-Me CF₃ 2-(3-Cl-pyridinyl) 196-197 D180 CH(CH₃)CH₂OCH₃ H 2-Cl CF₃ 2-(3-Cl-pyridinyl) 197-198 D181 CH(CH₃)CH₂SCH₃ H 2-Cl CF₃ 2-(3-Cl-pyridinyl) 202-203 D182 i-Pr H 2-Me CF₃ 2-IPh 221-222 D183 i-Pr H 2-Cl CF₃ 2-IPh 238-240 D184 i-Pr H 2-Me CF₃ 2-(C≡CH)—Ph 215-217 D185 i-Pr H 2-Cl CF₃ 2-(C≡CH)—Ph 244-246 D186 t-Bu H 2-Cl CF₃ 2-(3-Cl-pyridinyl) 250-251 D187

H 2-Cl CF₃ 2-(3-Cl-pyridinyl) >250 D188 i-Pr H 2-Me CF₃ 2-Cl-4-FPh 203-205 D189 i-Pr H 2-Cl CF₃ 2-Cl-4-FPh 218-219 D190 Me Me 2-Me CF₃ 2-ClPh 225-226 D191 Et Et 2-Me CF₃ 2-ClPh 243-247 D192 i-Pr H 2-Me CF₃ 2,6-Me₂Ph 259-260 D193 i-Pr H 2-Cl CF₃ 2,6-Me₂Ph 268-269 D194 i-Pr H 2-Me CF₃ 2,6-Cl₂-4-CNPh * D195 i-Pr H 2-Me CF₃ 2-CNPh 225-235 D196 i-pr H 2-Me CF₃ 2-(OCF₃)Ph 214-215 D197 i-Pr H 2-Cl CF₃ 2-(OCF₃)Ph 223-224 D198 i-pr H 2-Me CF₃ 2-Br-4-FPh 202-203 D199 i-Pr H 2-Cl CF₃ 2-Br-4-FPh 222-223 D200 i-Pr H 2-Me CF₃ 2-(3-Me-pyrazinyl) 205-207 D201 Me H 2-Cl CF₃ 2-(3-Cl-pyridinyl) 215-220 D202 CH₂C≡CH H 2-Cl CF₃ 2-(3-Cl-pyridinyl) 197-198 D203 Me H 2-Me CF₃ 2-(3-Cl-pyridinyl) 193-196 D204 Et H 2-Me CF₃ 2-(3-Cl-pyridinyl) 204-206 D205 CH₂C≡CH H 2-Me CF₃ 2-(3-Cl-pyridinyl) 177-178 D206 i-Pr H 2-Me CF₃ 4-(8-Cl-quinolinyl) >250 D207 i-Pr H 2-Me CF₃ 4-(2-Me-quinolinyl) >250 D208 i-Pr H 2-Cl CF₃ 4-(2-Me-quinolinyl) >250 D209 i-Pr H 2-Me CF₃ 4-(7-Cl-quinolinyl) >250 D210 i-Pr H 2,4-Br₂ CF₃ 2-ClPh 233-234 D211 i-Pr H 2-Br Br 2-ClPh 255-258 D212 Me H 2-Me Br 2-ClPh 236-237 D213 t-Bu H 2-Cl Br 2-ClPh 260-261 D214 Et H 2-Me Br 2-ClPh 254-255 D215 t-Bu H 2-Me Br 2-ClPh 259-260 D216 c-Bu H 2-Cl CN 2-(3-Cl-pyridinyl) 177-180 D217 i-Pr H 2-Me CF₃ 2-(3-Cl-pyridinyl) 237-239 D218 i-Pr H 2-Me CF₃ 2-(3-Cl-quinolinyl) >250 D219 Me Me 2-Me CF₃ 4-(6-Cl-quinolinyl) >250 D220 O-i-Pr H 2-Cl CF₃ 2-ClPh 218-219 D221 i-Pr H 2-Cl CN 2-(3-Cl-pyridinyl) 195-200 D222 t-Bu H 2-Cl CN 2-(3-Cl-pyridinyl) >250 D223 Et H 2-Cl CN 2-(3-Cl-pyridinyl) 200-205 D224 i-Pr H 2-Cl CF₃ 2-(3-Me-pyrazinyl) 225-230 D225 t-Bu H 2-Cl CF₃ 2-(3-Me-pyrazinyl) 235-240 D226 Et H 2-Cl CF₃ 2-(3-Me-pyrazinyl) 210-220 D227 i-Pr H 2-Me CF₃ 3-(2-Cl-pyridinyl) * D228 i-Pr H 2-Cl CF₃ 2,3-Cl₂Ph 217-219 D229 t-Bu H 2-Cl CF₃ 2,3-Cl₂Ph 254-256 D230 i-Pr H 2-Me CF₃ 2,3-Cl₂Ph 208-209 D231 t-Bu H 2-Me CF₃ 2,3-Cl₂Ph 232-233 D232 t-Bu H 2-Me-4-Br Br 2-ClPh 239-241 D233 Me H 2-Me-4-Br Br 2-ClPh 150-152 D234 Et H 2-Me-4-Br Br 2-ClPh 223-225 D235 i-Pr H 2-Me-4-Br Br 2-ClPh 197-198 D236 Me H 2-Me CF₃ 2-FPh 245-247 D237 CH₂C≡CH H 2-Me CF₃ 2-FPh 222-227 D238 O-i-Pr H 2-Cl CN 2-(3-Cl-pyridinyl) 205-206 D239 O-i-Pr H 2-Me CN 2-(3-Cl-pyridinyl) 210-211 D240 Me Me 2-Cl CF₃ 2-ClPh 234-236 D241 CH₂C≡CH H 2-Me-4-Br Br 2-ClPh 187-188 *See Index Table Q for ¹H NMR data

TABLE E INDEX

Com- pound R² R³ (R⁴)_(n) R⁷(a) R⁷(b) R⁷(c) m.p. ° C. E1 i-Pr H 2-Me CH₃ CH₃ H 143-145 E2 i-Pr H 2-Me CH₃ CH₂CF₃ H 198-199 E3 i-Pr H 2-Me CH₃ CH₃ Cl 188-190 E4 i-Pr H 2-Me CH₃ 4-CF₃—Ph H 198-199 E5 i-Pr H 2-Me CH₃ 2-CF₃—Ph H 211-213 E6 i-Pr H 2-Me CH₃ t-Bu H 125-127 E7 i-Pr H 2-Me CF₃ CH₂Ph H 130-135 E8 i-Pr H 2-Me H Ph CH₃ 249-250 E9 i-Pr H 2-Me H CH₃ Ph 268-270 E10 i-Pr H 2-Cl H Ph CH₃ 260-261 E11 i-Pr H 2-Me H CH₂CF₃ Ph 213-215 E12 i-Pr H 2-Cl H CH₂CF₃ Ph 208-209 E13 i-Pr H 2-Me H CHF₂ Ph * E14 i-Pr H 2-Me CF₃ 2-(3-Cl-pyridinyl) H 249-250 *See Index Table Q for ¹H NMR data

TABLE F INDEX

Com- pound R² R³ (R⁴)_(n) R⁷(a) R⁷(b) R⁷(c) m.p. ° C. F1 i-Pr H 2-Me CH₂CF₃ CH₃ H 254-255 F2 i-Pr H 2-Me CH₂CF₃ H CH₃ 200-205 F3 i-Pr H 2-Me CH₂(3-CF₃)Ph H CH₃ 212-215 F4 i-Pr H 2-Cl CH₂CF₃ H CH₃ 215-217 F5 i-Pr H 2-Me Ph H CF₃ 223-224 F6 i-Pr H 2-Cl Ph H CF₃ 206-208 F7 i-Pr H 2-Me CH₂CF₃ H Ph 156-158 F8 i-Pr H 2-Cl CH₂CF₃ H Ph 162-164

TABLE G INDEX

Compound Q R² R³ (R⁴)_(n) R⁷(a) R⁷(b) m.p. ° C. G1 S i-Pr H 2-Me 4-OCF₃Ph CH₃ 233-234 G2 S i-Pr H 2-Me OCH₂CF₂CF₃ CH₃ 170-173 G3 S i-Pr H 2-Me Cl CH₃ 164-167 G4 S i-Pr H 2-Me CH₃ Ph 216-219 G5 S i-Pr H 2-Me C(CH₃)₂OH CH₃ * G6 S i-Pr H 2-Me i-Pr CH₃ 180-181 G7 S i-Pr H 2-Me i-Pr Ph 182-183 G8 O i-Pr H 2-Me i-Pr CH₃ 163-164 *See Index Table Q for ¹H NMR data

TABLE H INDEX

Compound Q R² R³ (R⁴)_(n) R⁷(a) R⁷(b) R⁷(c) m.p. ° C. H1 S i-Pr H 2-Me H H H 192-195 H2 S CH(CH₃)CH₂OCH₃ H 2-Me H H H 120-123 H3 S t-Bu H 2-Me H H H 120-123 H4 NMe i-Pr H 2-Me Me H H 193-195 H5 NPh i-Pr H 2-Me H Me H 188-192 H6 NPh i-Pr H 2-Me Br H H 176-179 H7 NPh i-Pr H 2-Me Br H Br 215-216 H8 NPh i-Pr H 2-Me H H Br 150-154 H9 NPh i-Pr H 2-Me CF₃ H H 182-184  H10 N(2-ClPh) i-Pr H 2-Me Br H H 100-110  H11 N(2-FPh) i-Pr H 2-Me Br H H 178-179  H12 N(2-FPh) t-Bu H 2-Me Br H H 186-188  H13 N(2-ClPh) t-Bu H 2-Me Br H H 225-229

TABLE J INDEX

Compound R² R³ (R⁴)_(n) R⁷(a) R⁷(b) m.p. ° C. J1 i-Pr H 2-Me Me Me 221-222 J2 i-Pr H H CF₃ Ph 279-281 J3 i-Pr H 2-Me CF₃ Ph 263-268 J4 i-Pr H 2-Cl CF₃ 2-Clph 235-238 J5 i-Pr H 2-Cl CF₃ Ph 245-246 J6 i-Pr H 2-Me CF₃ 2-ClPh 240-242 J7 i-Pr H 2-Cl CF₃ 2-F-4-ClPh 246-247 J8 i-Pr H 2-Me CF₃ 2-F-4-ClPh 266-268 J9 i-Pr H 2-Me CF₃ 2-pyridinyl 258-260

TABLE K INDEX

Compound R² R³ (R⁴)_(n) R⁷(a) R⁷(b) m.p. ° C. K1 i-Pr H 2-Me Br H 177-180 K2 t-Bu H 2-Me Br H 188-194

TABLE L INDEX

Compound R² R³ (R⁴)_(n) R⁷(a) R⁷(b) m.p. ° C. L1 i-Pr H 2-Me Me Me 203-205 L2 i-Pr H 2-Me Me 2,6-Cl₂Ph 218-223

TABLE M INDEX

Compound Q R² R³ (R⁴)_(n) R⁷(a) R⁷(b) R⁷(c) m.p. ° C. M1 S i-Pr H 2-Me Cl Me H 203-205 M2 S i-Pr H 2-Cl Cl Me H 210-213 M3 NCHF₂ t-Bu H 2-Me H H Ph 165-166 M4 NH i-Pr H 2-Me CF₃ Ph H 118-120 M5 NMe i-Pr H 2-Me CF₃ Ph H 110-112 M6 NCHF₂ i-Pr H 2-Me 2-FPh H H 143-144 M7 NCHF₂ t-Bu H 2-Me 2-FPh H H 120-123 M8 NCH₂CF₃ i-Pr H 2-Me 2-FPh H H 235-237

TABLE N INDEX

Compound Het m.p. ° C. N1

169-171 N2

227-230 N3

243-246

TABLE P INDEX Compound m.p. ° C. P1

169-179

INDEX TABLE Q Compd. No. ¹H NMR Data (CDCl₃ solution unless indicated otherwise)^(a) D194 (DMSO-d6) δ 1.03 (d, 6H), 2.18(s, 3H), 3.92(m, 1H), 7.22-7.30 (m, 2H), 7.35(m, 1H), 7.62(dd, 1H), 7.81(s, 1H), 8.02(d, 1H), 8.15(dd, 1H), 8.55(dd, 1H), 10.34(s, 1H). D227 (DMSO-d6) δ 1.01(d, 6H), 2.16(s, 3H), 3.92(m, 1H), 7.27(m, 2H), 7.35(m, 1H), 7.89(s, 1H), 7.96(m, 1H), 8.37(s, 2H), 10.42(s, 1H). G5 δ 1.22 (d, 6H), 2.05(s, 6H), 2.31(s, 3H), 2.76(s, 3H), 4.18(m, 1H), 5.94(d, 1H), 7.20(dd, 1H), 7.29(d, 1H), 7.38(d, 1H), 9.83(br s, 1H). E13 δ 1.12(d, 6H), 2.32(s, 1H), 4.14(m 1H), 4.95(d, 1H), 7.19(dd, 1H), 7.28(t, 1H), 7.32(m, 5H), 7.59(dd, 2H), 7.92(s, 1H), 9.51(br s, 1H). ^(a1)H NMR data are in ppm downfield from tetramethylsilane. Couplings are designated by (s)-singlet, (d)-doublet, (t)-triplet, (q)-quartet, (m)-multiplet, (dd)-doublet of doublets, (dt)-doublet of triplets, (br s)-broad singlet.

BIOLOGICAL EXAMPLES OF THE INVENTION TEST

Application: Compounds are formulated in a 10% acetone, 90% water and 300 ppm X-77 surfactant solution, unless otherwise indicated. The formulated compounds are applied with a SUJ2 atomizer nozzle with ⅛ JJ custom body (Spraying Systems) positioned ½″ above the top of each test unit. There are 6 of these nozzles that make up the spray boom and this is fixed in a belt sprayer. A rack (or carrier) of 6 different insect test units is placed on the conveyor belt and stops so that each unit is centered under a nozzle. Once the rack is centered, 1 mL of liquid is sprayed into each test unit; the rack then continues down the belt to the end of the sprayer to be off-loaded. All experimental compounds in this screen are sprayed at 250 ppm and replicated three times.

Diamondback Moth (DBM)—Plutella Xylostella: The test unit consists of a small self-contained unit with a 12-14 day old radish plant inside. These are pre-infested (using a core sampler) with 10-15 neonate larvae on a piece of insect diet. Once 1 mL of formulated compound has been sprayed into each test unit, the test units are allowed to dry for 1 hour before a black, screened cap is placed on the top of the cylinder. They are held for 6 days in a growth chamber at 25° C. and 70% relative humidity.

Plant feeding damage was visually assessed on a scale of 0-10 where 0 is no feeding, 1 is 10% or less feeding, 2 is 20% or less feeding, 3 is 30% or less feeding through a maximum score of 10 where 10 is 100% of foliage consumed. Of the compounds tested the following provided excellent levels of plant protection (ratings of 0-1, 10% or less feeding damage): 1, 2, 3, 4, 6, 7, 9, 10, 13, 14, 15, 19, 20, 24, 27, 28, 29, 30, 31, 32, 33, 35, 37, 38, 39, 51, 52, 53, 60, 61, 62, 63, 64, 65, 66, 68, 69, 72, 73, 74, 75, 76, 79, 80, 84, 86, 88, 89, 90, 92, 96, 97, 98, 99, 100, 101, 102, 103, 107, 113, 124, 126, 127, 143, 144, 146, 147, 148, 150, 151, 152, 153, 158, 159, 160, 161, 162, 163, 164, 165, 166, 167, 169, 170, 171, 174, 183, 184, 185, 186, 187, 188, 189, 190, 191, 193, 194, 195, 196, 198, 202, 203, 204, 205, 206, 207, 208, 209, 210, 211, 212, 213, 214, 215, 216, 217, 218, 219, 220, 222, 223, 225, 227, 228, 229, 230, 231, 232, 233, 235, 238, 239, 240, 244, 245, 246, 248, 249, 250, 251, 252, 253, 256, 257, 275, 276, 277, 278, B2, B4, B5, B6, B7, B8, B9, B10, B11, B12, B13, B14, B15, B16, B17, B18, B19, B20, B21, B23, B24, B25, B28, B29, B30, B31, B32, B33, B35, B37, B38, B39, B40, B42, B43, B44, B45, B46, B47, B48, B49, B50, B53, B55, B57, B58, B59, B60, B61, B62, B63, B64, B66, B67, B68, B69, B70, B71, B72, B74, B75, B76, C1, C2, C3, C4, C5, C7, C8, C9, C10, C11, C12, C79, D2, D3, D4, D5, D6, D7, D8, D11, D12, D13, D14, D15, D16, D18, D19, D20, D23, D24, D25, D26, D27, D28, D29, D30, D32, D33, D34, D37, D38, D39, D40, D41, D42, D45, D46, D47, D48, D50, D51, D52, D53, D54, D55, D56, D57, D58, D59, D60, D61, D62, D63, D64, D65, D66, D67, D68, D69, D70, D71, D72, D73, D74, D75, D76, D77, D78, D79, D81, D83, D84, D85, D86, D87, D88, D89, D91, D92, D93, D94, D95, D96, D97, D111, D113, D114, D115, D116, D117, D118, D119, D120, D121, D122, D123, D124, D125, D126, D162, D164, E4, F2, F5, F6, F7, F8, G2, G3, G5, H1, H2, H3, H4, J3, J4, J6, M1, M3, N2 and P1. 

What is claimed is:
 1. A method for controlling arthropods comprising contacting the arthropods or their environment with an arthropodicidally effective amount of a compound of Formula 1, its N-oxide or agriculturally suitable salts

wherein A and B are independently O or S; each J is independently a 5-membered heteroaromatic ring wherein each ring is optionally substituted with 1 to 4 R⁷; n is 1 to 4; R¹ is H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆ cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₄ alkoxycarbonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino and C₃-C₆ cycloalkylamino; or R¹ is C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C(═A)J; R² is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ alkoxy, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆ alkoxycarbonyl or C₂-C₆ alkylcarbonyl; R³ is H; G; C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, each optionally substituted with one or more substituents selected from the group consisting of halogen, G, CN, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylcarbonyl, C₃-C₆ trialkylsilyl, and a phenyl, phenoxy or 5- or 6-membered heteroaromatic ring, each ring optionally substituted with one to three substituents independently selected from the group consisting of C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl and C₃-C₆ trialkylsilyl; C₁-C₄ alkoxy; C₁-C₄ alkylamino; C₂-C₈ dialkylamino; C₃-C₆ cycloalkylamino; C₂-C₆ alkoxycarbonyl or C₂-C₆ alkylcarbonyl; G is a 5- or 6-membered nonaromatic carbocyclic or heterocyclic ring, optionally including one or two ring members selected from the group consisting of C(═O), SO or S(O)₂ and optionally substituted with 1 to 4 substituents selected from the group consisting of C₁-C₂ alkyl, halogen, CN, NO₂ and C₁-C₂ alkoxy; each R⁴ is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, or C₃-C₆ trialkylsilyl; or each R⁴ is independently phenyl, benzyl or phenoxy, each optionally substituted with C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl; each R⁷ is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, CO₂H, CONH₂, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl, or C₃-C₆ trialkylsilyl; or each R⁷ is independently a phenyl, benzyl, benzoyl, phenoxy, 5- or 6-membered heteroaromatic ring or an aromatic 8-, 9- or 10-membered fused heterobicyclic ring system, each ring optionally substituted with one to three substituents independently selected from the group consisting of C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl and C₃-C₆ trialkylsilyl; provided that J is other than an optionally substituted 1,2,3-thiadiazole.
 2. The method of claim 1 wherein J is a 5-membered heteroaromatic ring optionally substituted with 1 to 4 R⁷.
 3. The method of claim 2 wherein J is a 5-membered heteroaromatic ring selected from the group consisting of J-1, J-2, and J-3, wherein J-3 is substituted with R⁷

Q is O, S or NR⁷; and X, Y and Z are independently N or CR⁷.
 4. The method of claim 2 or 3 wherein A and B are O; n is 1 to 2; R¹ is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl; R² is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl; R³ is H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆ cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, C₁-C₂ alkoxy, C₁-C₂ alkylthio, C₁-C₂ alkylsulfinyl and C₁-C₂ alkylsulfonyl; one of the R⁴ groups is attached to the phenyl ring at the 2-position, and said R⁴ is C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl or C₁-C₄ haloalkylsulfonyl; and each R⁷ is independently H, C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen, CN, NO₂, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl or C₂-C₄ alkoxycarbonyl; or a phenyl or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl.
 5. The method of claim 4 wherein J is selected from the group consisting of pyrazole, imidazole, triazole, thiophene, thiazole, oxazole, furan, isothiazole and isoxazole, each optionally substituted with 1 to 3 R⁷.
 6. The method of claim 5 wherein J is selected from the group consisting of pyrazole, thiophene and thiazole, each optionally substituted with 1 to 3 R⁷; R¹ and R² are both H; R³ is C₁-C₄ alkyl optionally substituted with halogen, CN, OCH₃, or S(O)_(p)CH₃; each R⁴ is independently H, CH₃, CF₃, OCF₃, OCHF₂, S(O)_(p)CF₃, S(O)_(p)CHF₂, CN or halogen; each R⁷ is independently H, halogen, CH₃, CF₃, OCHF₂, S(O)_(p)CF₃, S(O)_(p)CHF₂, OCH₂CF₃, OCF₂CHF₂, S(O)_(p)CH₂CF₃, S(O)_(p)CF₂CHF₂; or phenyl, pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, halogen or CN; and p is 0, 1 or
 2. 7. The method of claim 6 wherein J is a pyrazole optionally substituted with 1 to3 R⁷.
 8. The method of claim 7 wherein one R⁷ is a phenyl optionally substituted with C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen or CN.
 9. The method of claim 7 wherein one R⁷ is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen or CN.
 10. The method of claim 9 wherein R⁷ is a pyridine optionally substituted with C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen or CN.
 11. The method of claim 1 comprising a compound of Formula 1 selected from the group consisting of: 1-ethyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide, 1-(2-fluorophenyl)-N-[2-methyl-6-[[(1-methylethyl)amino)carbonyl]phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide, 1-(3-chloro-2-pyridinyl)-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]3-(trifluoromethyl)-1H-pyrazole-5-carboxamide, N-[2-chloro-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide, 3-bromo-1-(2-chlorophenyl)-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1H-pyrazole-5-carboxamide, and 3-bromo-N-[2-chloro-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1-(2-chlorophenyl)-1H-pyrazole-5-carboxamide.
 12. A compound of Formula 1, its N-oxides and agriculturally suitable salts

wherein A and B are independently O or S; each J is independently a 5-membered heteroaromatic ring wherein each ring is optionally substituted with 1 to 4 R⁷; n is 1 to 4; R¹ is H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆ cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₄ alkoxycarbonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino and C₃-C₆ cycloalkylamino; or R¹ is C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C(═A)J; R² is H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ alkoxy, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆ alkoxycarbonyl or C₂-C₆ alkylcarbonyl; R³ is H; C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylcarbonyl, C₃-C₆ trialkylsilyl, and a phenoxy ring optionally substituted with one to three substituents independently selected from the group consisting of C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl and C₃-C₆ trialkylsilyl; C₁-C₄ alkoxy; C₁-C₄ alkylamino; C₂-C₈ dialkylamino; C₃-C₆ cycloalkylamino; C₂-C₆ alkoxycarbonyl or C₂-C₆ alkylcarbonyl; each R⁴ is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, or C₃-C₆ trialkylsilyl; or each R⁴ is independently phenyl, benzyl or phenoxy, each optionally substituted with C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl; each R⁷ is independently H, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl, C₃-C₆ cycloalkyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₂-C₆ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, CO₂H, CONH₂, NO₂, hydroxy, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₂-C₆ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl, or C₃-C₆ trialkylsilyl; or each R⁷ is independently a phenyl, benzyl, benzoyl, phenoxy or 5- or 6-membered heteroaromatic ring or an 8-, 9- or 10-membered fused heterobicyclic ring system, each ring optionally substituted with one to three substituents independently selected from the group consisting of C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl and C₃-C₆ trialkylsilyl; provided that (i) at least one R⁴ and at least one R⁷, when R⁷ is present, are other than H; (ii) J is other than an optionally substituted 1,2,3-thiadiazole; (iii) when J is an optionally substituted pyrazole or tetrazole, then R² and R³ cannot both be hydrogen; (iv) when J is an optionally substituted tetrazole, then R⁷ is other than an optionally substituted benzyl.
 13. The compound of claim 12 wherein J is a 5-membered heteroaromatic ring selected from the group consisting of J-1, J-2, and J-3, wherein J-3 is substituted with R⁷

Q is O, S or NR⁷; and X, Y and Z are independently N or CR⁷.
 14. The compound of claim 13 wherein A and B are O; n is 1 to 2; R¹ is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl; R² is H, C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₂-C₆ alkylcarbonyl or C₂-C₆ alkoxycarbonyl; R³ is H; or C₁-C₆ alkyl, C₂-C₆ alkenyl, C₂-C₆ alkynyl or C₃-C₆ cycloalkyl each optionally substituted with one or more substituents selected from the group consisting of halogen, CN, C₁-C₂ alkoxy, C₁-C₂ alkylthio, C₁-C₂ alkylsulfinyl and C₁-C₂ alkylsulfonyl; one of the R⁴ groups is attached to the phenyl ring at the 2-position, and said R⁴ is C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl or C₁-C₄ haloalkylsulfonyl; and each R⁷ is independently H, C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen, CN, NO₂, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ haloalkylthio, C₁-C₄ haloalkylsulfinyl, C₁-C₄ haloalkylsulfonyl or C₂-C₄ alkoxycarbonyl; or a phenyl or a 5- or 6-membered heteroaromatic ring, each ring optionally substituted with C₁-C₄ alkyl, C₂-C₄ alkenyl, C₂-C₄ alkynyl, C₃-C₆ cycloalkyl, C₁-C₄ haloalkyl, C₂-C₄ haloalkenyl, C₂-C₄ haloalkynyl, C₃-C₆ halocycloalkyl, halogen, CN, NO₂, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, C₁-C₄ alkylamino, C₂-C₈ dialkylamino, C₃-C₆ cycloalkylamino, C₃-C₆ (alkyl)cycloalkylamino, C₂-C₄ alkylcarbonyl, C₂-C₆ alkoxycarbonyl, C₂-C₆ alkylaminocarbonyl, C₃-C₈ dialkylaminocarbonyl or C₃-C₆ trialkylsilyl.
 15. The compound of claim 14 wherein J is selected from the group consisting of pyrazole, imidazole, triazole, thiophene, thiazole and oxazole, furan, isothiazole and isoxazole, each optionally substituted with 1 to 3 R⁷.
 16. The compound of claim 15 wherein J is selected from the group consisting of pyrazole, thiophene and thiazole, each optionally substituted with 1 to 3 R⁷; R¹ and R² are both H; R³ is C₁-C₄ alkyl optionally substituted with halogen, CN, OCH₃, S(O)_(p)CH₃; each R⁴ is independently H, CH₃, CF₃, OCF₃, OCHF₂, S(O)_(p)CF₃, S(O)_(p)CHF₂, CN or halogen; each R⁷ is independently H, halogen, CH₃, CF₃, OCHF₂, S(O)_(p)CF₃, S(O)_(p)CHF₂, OCH₂CF₃, OCF₂CHF₂, S(O)_(p)CH₂CF₃, S(O)_(p)CF₂CHF₂; or phenyl, pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with C₁-C₄ alkyl, C₁-C₄ haloalkyl, C₁-C₄ alkoxy, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ alkylsulfinyl, C₁-C₄ alkylsulfonyl, halogen or CN; and p is 0, 1 or
 2. 17. The compound of claim 16 wherein J is a pyrazole optionally substituted with 1 to 3 R⁷.
 18. The compound of claim 17 wherein one R⁷ is a phenyl optionally substituted with C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen or CN.
 19. The compound of claim 17 wherein one R⁷ is a pyrazole, imidazole, triazole, pyridine or pyrimidine, each ring optionally substituted with C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen or CN.
 20. The compound of claim 17 wherein R⁷ is a pyridine optionally substituted with C₁-C₄ alkyl, C₁-C₄ haloalkyl, halogen or CN.
 21. The compound of claim 12 selected from the group consisting of: 1-ethyl-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide, 1-(2-fluorophenyl)-N-[2-methyl-6-[[(1-methylethyl)amino)carbonyl]phenyl]-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide, 1-(3-chloro-2-pyridinyl)-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]3-(trifluoromethyl)-1H-pyrazole-5-carboxamide, N-[2-chloro-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1-(3-chloro-2-pyridinyl)-3-(trifluoromethyl)-1H-pyrazole-5-carboxamide, 3-bromo-1-(2-chlorophenyl)-N-[2-methyl-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1H-pyrazole-5-carboxamide, and 3-bromo-N-[2-chloro-6-[[(1-methylethyl)amino]carbonyl]phenyl]-1-(2-chlorophenyl)-1H-pyrazole-5-carboxamide.
 22. An arthropodicidal composition comprising an arthropodicidally effective amount of a compound of Formula 1 as described in claim 1 and at least one additional component selected from the group consisting of surfactants, solid diluents and liquid diluents. 